Aryl-substituted heterocyclic enaminones

ABSTRACT

The invention relates to novel heterocyclic enaminones of the general formula (I)  
                 
 
in which Ar, Z, K, X, y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6  and V are as defined in the description, to their use as herbicides, acaricides and insecticides, and to processes for their preparation.

The invention relates to novel aryl-substituted heterocyclic enaminones,to a plurality of processes for their preparation, to intermediates, andto the use of the enaminones as crop protection agents, in particular asherbicides, acaricides, nematicides and insecticides.

Certain carbocyclic enaminones which are substituted in the phenyl ringhave already been disclosed as intermediates for antibacterially activequinolones (R. G. Glushkov, N. B. Marchenko, A. N. Padeiskaya, L. D.Shipilova, Pharm. Chem. J. (Engl. Transl.) 24, 460-465, (1990)). Alsoknown are carbocyclic enaminones which are unsubstituted in the phenylring (M. V. Mezentseva, A. V. Kadushkin, L. M. Alekseeva, A. S.Sokolova, V. G. Granik, Pharm. Chem. J. (Engl. Transl.) 25, 858-864(1991); G. M. Coppola, R. Damon, A. D. Kahle, M. J. Shapiro, J. Org.Chem. 46, 1221-1222, (1981); D. Brillon, G. Sauvé, J. Org. Chem. 55,2246-2249, (1990)). The use of these compounds as crop protection agentshas hitherto not been described.

In a general manner, the novel heterocyclic enaminones are described bythe formula (I)

in which

K represents oxygen or sulphur,

Ar represents in each case substituted phenyl, naphthyl or represents ineach case optionally substituted mono- or bicyclic hetaryl having 5 to10 ring atoms,

V represents oxygen or represents the groups —S(O)_(n)— or >N—W,

W represents hydrogen, optionally substituted alkyl, alkenyl, alkinyl,cycloalkyl, cycloalkyl-alkyl, alkoxyalkyl, alkoxy, phenylalkyloxy,phenyl, phenylalkyl, hetaryl, hetarylalkyl or represents the groups—COR¹,

Y¹ and Y³ independently of one another represent hydrogen, halogen or ineach case optionally substituted alkyl, alkoxy, alkoxyalkyl, phenyl,phenylalkyl, hetaryl, hetarylalkyl or represent the groups

Y², Y⁴, Y⁶ independently of one another represent hydrogen, halogen oroptionally substituted alkyl,

Y⁵ represents hydrogen or in each case optionally substituted alkyl orphenyl, or

Y⁴ and Y⁵ together with the carbon atoms to which they are attachedrepresent an optionally substituted saturated or unsaturated cycle whichis optionally interrupted by heteroatoms, or

Y¹ and Y² together with the carbon atom to which they are attachedrepresent an optionally substituted saturated or unsaturated cycle whichis optionally interrupted by heteroatoms,

Z represents hydrogen, represents in each case optionally substitutedalkyl, alkenyl, alkinyl, cycloalkyl, cycloalkyl-alkyl, alkoxyalkyl,phenoxyalkyl, phenylalkyl-oxyalkyl, phenylthioalkyl,phenylalkyl-thioalkyl, phenyl, phenylalkyl, hetaryl, hetaryl-alkyl orrepresents the groups

or cyano,

l represents 0 to 3,

m represents 0 to 2,

n represents 0 to 2,

R¹ represents hydrogen, represents in each case optionally substituted,saturated or unsaturated alkyl or cycloalkyl, each of which isoptionally interrupted by heteroatoms, represents in each caseoptionally substituted phenyl or hetaryl, represents in each caseoptionally substituted phenylalkyl or hetarylalkyl,

R² represents hydrogen, represents in each case optionally substituted,saturated or unsaturated alkyl or alkoxy, represents in each caseoptionally substituted phenyl, phenylalkyl or phenylalkyloxy,

R¹, R² furthermore together with the nitrogen atom to which they areattached may represent an optionally substituted cycle which isoptionally interrupted by heteroatoms, or

R³ represents hydrogen, represents in each case optionally substitutedalkyl or alkoxy, represents in each case optionally substituted phenylor phenylalkyl,

R⁴ represents hydrogen or represents optionally substituted alkyl, andR⁵, R⁶ independently of one another represent hydrogen or representoptionally substituted alkyl.

For the compounds of the formula (I):

Ar preferably represents Ar¹, where Ar¹ represents phenyl, naphthyl ormono- or bicyclic hetaryl having five to ten ring atoms, each of whichradicals is optionally mono- to pentasubstituted by halogen,C₁-C₈-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkinyl, C₁-C₈-alkoxy,C₂-C₈-alkenyloxy, C₃-C₈-alkinyloxy, C₁-C₈-alkylthio,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkyl,C₁-C₆-halogeno-alkoxy, C₂-C₈-halogenoalkenyloxy,C₁-C₂-alkylidenediyl-dioxy, C₁-C₂-halogenoalkylidenediyl-dioxy,halogeno-C₁-C₄-alkylthio, halogeno-C₁-C₄-alkylsulphinyl,halogeno-C₁-C₄-alkylsulphonyl, hydroxyl, mercapto, nitro, cyano, aminoor by the groups

-   -   or represents Ar², where Ar² represents Ar¹ which is        additionally substituted by phenyl, naphthyl, five- or        six-membered hetaryl, phenyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy,        phenyl-C₁-C₄-alkyl-S(O)_(p)—, five- or six-membered        hetaryl-C₁-C₄-alkoxy, five- or six-membered        hetaryl-C₁-C₄-alkyl-S(O)_(p)—, phenoxy, phenyl-S(O)_(p)—, five-        or six-membered hetaryloxy or hetaryl-S(O)_(p)—, where these        substituents for their part are in each case optionally mono- to        tetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro or cyano.

K preferably represents oxygen or sulphur.

L preferably represents oxygen or sulphur.

V preferably represents oxygen or represents the groups —S(O)_(n)— or>N—W

W preferably represents hydrogen, represents in each case optionallyfluorine- and/or chlorine-substituted C₁-C₈-alkyl, C₃-C₈-alkenyl,C₃-C₈-alkinyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₂-alkyl,C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₂-C₄-alkyl, represents phenyl,C₁-C₄-phenylalkyl, C₁-C₄-phenylalkyloxy, hetaryl, hetarylalkyl, each ofwhich is optionally mono- to tetrasubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro or cyanoor represents the groups

-   -   or cyano.

X preferably represents CN,

Y¹ and Y³ independently of one another preferably represent hydrogen,halogen, C₁-C₆-alkyl, C₁-C₄-halogenoalkyl, C₁-C₆-alkoxy,C₁-C₆-alkoxy-C₁-C₂-alkyl, represent phenyl, phenyl-C₁-C₄-alkyl, five- orsix-membered hetaryl or five- or six-membered hetaryl-C₁-C₄-alkyl, eachof which is optionally mono- to tetrasubstituted by halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,cyano or nitro or represent the groups

Y², Y⁴, Y⁶ independently of one another preferably represent hydrogen,halogen or represent fluorine- and/or chlorine-substituted C₁-C₆-alkyl.

Y⁵ preferably represents hydrogen, represents optionallyfluorine-substituted C₁-C₆-alkyl or represents phenyl which isoptionally mono- to tetrasubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro.

Y⁴ and Y⁵ together with the carbon atoms to which they are attachedpreferably represent a 5- to 8-membered saturated or unsaturated cyclewhich may be interrupted by 1 to 3 heteroatoms from the group consistingof N, O, S and which may optionally be mono- to trisubstituted byhalogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, cyano or nitro.

Y¹ and Y² together with the carbon atom to which they are attachedpreferably represent a C₃-C₆-Cycloalkyl ring.

Z preferably represents hydrogen, represents in each case optionallyfluorine- and/or chlorine-substituted C₁-C₈-alkyl, cyano-C₁-C₆-alkyl,C₃-C₈-alkenyl, C₃-C₈-alkinyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₂-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-halogenoalkoxy-C₁-C₄-alkyl, represents phenoxy-C₁-C₄-alkyl,phenyl-C₁-C₄-alkyloxy-C₁-C₄-alkyl, phenylthio-C₁-C₄-alkyl,phenyl-C₁-C₄-alkylthio-C₁-C₄-alkyl, phenyl, phenyl-C₁-C₄-alkyl, five- orsix-membered hetaryl, five- or six-membered hetaryl-C₁-C₄-alkyl, each ofwhich is optionally mono- to tetrasubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro or cyanoor represents the groups

-   -   or cyano.

p preferably represents 0 to 2.

l preferably represents 0 to 2.

R¹ preferably represents hydrogen (but not in the radicals —CO₂R¹ and—SO₂R¹), represents in each case optionally fluorine- and/orchlorine-substituted C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₃-C₆-alkinyl,represents in each case optionally fluorine-, chlorine-, C₁-C₄-alkyl-,C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl, inwhich optionally one methylene group may be interrupted by oxygen orsulphur, or represents phenyl, pyridyl, thienyl, pyrimidyl, thiazolyl,phenyl-C₁-C₄-alkyl, pyridyl-C₁-C₂-alkyl, thiazolyl-C₁-C₂-alkyl, each ofwhich is optionally mono- to tetrasubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro.

R² preferably represents hydrogen, represents in each case optionallyfluorine- and/or chlorine-substituted C₁-C₆-alkyl, C₃-C₆-alkenyl,C₃-C₆-alkinyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy or represents phenyl,phenyl-C₁-C₄-alkyl or phenyl-C₁-C₄-alkoxy, each of which is optionallymono- to tetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro.

R¹, R² furthermore together with the nitrogen atom to which they areattached may preferably represent a five- to eight-membered cycle inwhich optionally one methylene group may be replaced by oxygen orsulphur and which may in each case optionally be substituted byC₁-C₄-alkyl.

R³ preferably represents hydrogen, optionally halogen-substitutedC₁-C₆-alkyl or represents phenyl or phenyl-C₁-C₂-alkyl, each of which isoptionally mono- to tetrasubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro.

R⁴ preferably represents hydrogen or C₁-C₆-alkyl.

R⁵, R⁶ preferably independently of one another represent hydrogen oroptionally fluorine- and/or chlorine-substituted C₁-C₄-alkyl.

R⁷ preferably represents in each case optionally fluorine- and/orchlorine-substituted C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₃-C₁₀-alkinyl,C₁-C₁₀-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, ineach case optionally fluorine-, chlorine-, C₁-C₄-alkyl- and/orC₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl or C₃-C₈-cycloalkoxy, in whichoptionally one methylene group may be replaced by oxygen or sulphur,represents phenyl, phenoxy, benzyloxy, five- or six-membered hetaryl orphenyl-C₁-C₄-alkyl, each of which may optionally be mono- totetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogeno-alkyl, C₁-C₄-halogenoalkoxy, cyano or nitro or, in thecase of the radicals a) and c) mentioned under Ar, also represents agroup

or, for the radical g), also represents hydroxyl.

R⁸ preferably represents hydrogen or C₁-C₄-alkyl.

R⁹ preferably represents hydrogen, in each case optionally fluorine-and/or chlorine-substituted C₁-C₁₀-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkinyl,C₁-C₁₀-alkoxy, C₃-C₈-alkenyloxy, optionally fluorine-, chlorine-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl, in whichoptionally one methylene group may be replaced by oxygen or sulphur,represents phenyl, phenyl-C₁-C₄-alkyl or phenyl-C₁-C₂-alkoxy, each ofwhich may optionally be mono- to tetrasubstituted by halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,cyano or nitro.

R¹⁰ preferably represents hydrogen, C₁-C₆-alkyl or C₃-C₆-alkenyl.

R⁹, R¹⁰ furthermore together with the nitrogen atom to which they areattached may preferably represent an optionally C₁-C₄-alkyl-substitutedfive- to eight-membered cycle in which optionally one methylene groupmay be replaced by oxygen or sulphur.

m preferably represents 0 to 2.

n preferably represents 0 to 2.

K particularly preferably represents oxygen or sulphur.

Ar particularly preferably represents Ar¹, where Ar¹ represents phenyl,naphthyl, quinolinyl, thienyl, pyrimidyl, furanyl, thiazolyl,benzothiazolyl, oxazolyl, pyrazolyl or pyridyl, each of which isoptionally mono- to trisubstituted by fluorine, chlorine, bromine,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkoxy,C₃-C₆-alkenyloxy, C₃-C₆-alkinyloxy, C₁-C₆-alkylthio,C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, C₂-C₄-halogenoalkenyloxy,C₁-C₂-alkylidenediyl-dioxy, C₁-C₂-halogenoalkylidenediyl-dioxy,halogen-C₁-C₂-alkylthio, halogen-C₁-C₂-alkylsulphinyl,halogen-C₁-C₂-alkylsulphonyl, hydroxyl, mercapto, nitro, cyano, amino orby one of the following groups

-   -   or particularly preferably represents Ar², where Ar² represents        Ar¹ which is additionally substituted by phenyl, pyridyl,        pyrimidyl, thienyl, furanyl, thiazolyl, tetrazolyl, triazolyl,        benzyl, phenyl-C₁-C₂-alkoxy, phenyl-C₁-C₂-alkyl-S(O)_(p)—,        thienyl-C₁-C₂-alkoxy, thiazolyl-C₁-C₂-alkoxy,        pyridyl-C₁-C₂-alkoxy, pyrimidyl-C₁-C₂-alkoxy,        thiazolyl-C₁-C₂-alkyl-S(O)_(p)—, pyridyl-C₁-C₂-alkyl-S(O)_(p),        phenoxy, phenyl-S(O)_(p)—, pyridyloxy, pyrimidyloxy,        thiazolyloxy, pyridyl-S(O)_(p)—, pyrimidyl-S(O)_(p)— or        thiazolyl-S(O)_(p)—, where these substituents for their part are        optionally mono- to trisubstituted by fluorine, chlorine,        bromine, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₁-C₄-alkoxy,        C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, nitro or cyano.

L particularly preferably represents oxygen or sulphur.

V particularly preferably represents oxygen or represents the groups—S(O)_(n)— or

W particularly preferably represents hydrogen, represents in each caseoptionally fluorine- and/or chlorine-substituted C₁-C₆-alkyl,C₃-C₆-alkenyl, C₃-C₆-alkinyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₂-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₂-C₃-alkyl,represents phenyl, phenyl-C₁-C₂-alkyl, phenyl-C₁-C₂-alkoxy, pyridyl,thiazolyl, pyrimidyl, thienyl, pyridyl-C₁-C₂-alkyl,pyrimidyl-C₁-C₂-alkyl, thiazolyl-C₁-C₂-alkyl, each of which isoptionally mono- to trisubstituted by fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,nitro or cyano or represents the groups

X particularly preferably represents CN,

Y¹ and Y³ independently of one another particularly preferably representhydrogen, optionally represent fluorine, C₁-C₄-alkyl,C₁-C₂-halogenoalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₂-alkyl, representphenyl, thienyl, pyridyl, thiazolyl, pyrimidyl, phenyl-C₁-C₂-alkyl,thiazolylmethyl, pyridylmethyl, each of which is optionally mono- totrisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, cyano or nitroor represent the groups

Y², Y⁴, Y⁶ independently of one another particularly preferablyrepresent hydrogen or C₁-C₄-alkyl.

Y⁵ particularly preferably represents hydrogen, represents optionallyfluorine-substituted C₁-C₄-alkyl or represents phenyl which isoptionally mono- to trisubstituted by fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,nitro or cyano.

Y⁴ and Y⁵ furthermore together with the carbon atoms to which they areattached particularly preferably represent a 5- or 6-membered saturatedor unsaturated cycle which may be interrupted by a heteroatom from thegroup consisting of N, O, S and which may optionally be mono- ordisubstituted by fluorine, chlorine, bromine, methyl, tert-butyl,methoxy, trifluoromethyl, tri-fluoromethoxy, cyano or nitro.

Y¹ and Y² together with the carbon atom to which they are attachedparticularly preferably represent a C₄-C₆-cycloalkyl ring.

Z particularly preferably represents hydrogen, represents in each caseoptionally fluorine- and/or chlorine-substituted C₁-C₆-alkyl,cyano-C₁-C₃-alkyl, C₃-C₆-alkenyl, C₃-C₈-alkinyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₂-alkyl, C₁-C₄-alkoxy-C₁-C₂-alkyl,C₁-C₄-halogeno-C₁-C₂-alkyl, represents phenoxy-C₁-C₂-alkyl,phenyl-C₁-C₂-alkyloxy-C₁-C₂-alkyl, phenylthio-C₁-C₂-alkyl,phenyl-C₁-C₂-alkylthio-C₁-C₂-alkyl, phenyl-C₁-C₂-alkyl, phenyl,pyridyl-C₁-C₂-alkyl, thiazolyl-C₁-C₂-alkyl, each of which is optionallymono- to trisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, nitro or cyanoor represents the groups

-   -   or cyano.

p particularly preferably represents 0 to 2.

R¹ particularly preferably represents hydrogen (but not in the radicals—CO₂R¹ and —SO₂R¹), represents in each case optionally fluorine- and/orchlorine-substituted C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₄-alkinyl,represents in each case optionally fluorine-, chlorine-, C₁-C₂-alkyl-,C₁-C₂-alkoxy-substituted C₃-C₆-cycloalkyl or represents phenyl orbenzyl, each of which is optionally mono- or disubstituted by fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, cyano or nitro.

R² particularly preferably represents hydrogen, represents in each caseoptionally fluorine- and/or chlorine-substituted C₁-C₄-alkyl,C₃-C₄-alkenyl, C₃-C₄-alkinyl, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy orrepresents phenyl, benzyl, benzyloxy, each of which is optionally mono-or disubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy cyano or nitro.

R¹, R² furthermore together with the nitrogen atom to which they areattached may particularly preferably represent an optionallyC₁-C₂-alkyl-substituted five- or six-membered cycle in which optionallyone methylene group may be replaced by oxygen.

R⁵ particularly preferably represents hydrogen, methyl or ethyl.

R⁷ particularly preferably represents C₁-C₆-alkyl, C₂-C₆-alkenyl,C₃-C₆-alkinyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₂-alkyl,C₁-C₄-alkylthio-C₁-C₂-alkyl, each of which is optionally substituted byfluorine and/or chlorine, represents C₃-C₆-cycloalkyl orC₃-C₆-cycloalkoxy in which optionally one methylene group may bereplaced by oxygen and which are in each case optionally substituted byfluorine, chlorine, C₁-C₂-alkyl and/or C₁-C₂-alkoxy, represents phenyl,phenoxy, benzyloxy, thienyl, furanyl, pyridyl, pyrimidyl, thiazolyl,pyrazolyl or phenyl-C₁-C₂-alkyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro or,in the case of the radicals a) and c) mentioned under Ar, alsorepresents a group

or, for the radical g), also represents hydroxyl.

R⁸ particularly preferably represents hydrogen.

R⁹ particularly preferably represents hydrogen, represents C₁-C₆-alkyl,C₃-C₆-alkenyl, C₃-C₆-alkinyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, in whichoptionally one methylene group may be replaced by oxygen and each ofwhich is optionally substituted by fluorine and/or chlorine, representsphenyl or phenyl-C₁-C₂-alkyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro.

R¹⁰ particularly preferably represents hydrogen or C₁-C₄-alkyl.

R⁹, R¹⁰ furthermore together with the nitrogen atom to which they areattached may particularly preferably represent an optionallyC₁-C₂-alkyl-substituted five- or six-membered cycle in which optionallyone methylene group may be replaced by oxygen.

m particularly preferably represents 0 or 1.

n particularly preferably represents 0 to 2.

K very particularly preferably represents oxygen or sulphur.

Ar very particularly preferably represents Ar¹, where Ar¹ representsphenyl, thienyl, pyrimidyl, furanyl or pyridyl, each of which isoptionally mono- to trisubstituted by fluorine, chlorine, bromine,methyl, ethyl, propyl, i-propyl, s-, n-, i- or t-butyl, methoxy, ethoxy,propoxy, i-propoxy, s-, n-, i- or t-butoxy, allyloxy, methallyloxy,2-butenyloxy, propargyloxy, 2-butinyloxy, methylthio, ethylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl,trifluoromethyl, difluoromethoxy, trifluoromethoxy, methylenedioxy,difluoromethylenedioxy, tetrafluoroethylenedioxy, difluoromethylthio,trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl,hydroxyl, mercapto, nitro, cyano, amino, or by one of the followinggroups

or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl, pyridyl, thienyl, tetrazolyl, triazolyl,benzyloxy, benzylthio, thiazolylmethyloxy, pyridylmethyloxy,pyrimidylmethyloxy, thiazolylmethylthio, pyridylmethylthio, phenoxy orphenylthio, where these substituents for their part are optionally mono-or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, n- ori-propyl, s-, n-, i- or t-butyl, methoxy, ethoxy, i-propoxy, s-, n- ort-butoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano.

L very particularly preferably represents oxygen or sulphur.

V very particularly preferably represents oxygen or sulphur.

X very particularly preferably represents —CN, —CO—NH₂,

Y¹ and Y³ independently of one another very particularly preferablyrepresent hydrogen, methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl,sec-butyl, tert-butyl, represent phenyl or benzyl, each of which isoptionally mono- to trisubstituted by fluorine, chlorine, bromine,methyl, methoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy.

Y², Y⁴, Y⁶ independently of one another very particularly preferablyrepresent hydrogen, methyl or ethyl.

Y⁵ very particularly preferably represents hydrogen, methyl, ethyl,propyl, i-propyl or represents phenyl which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, ethyl, i-propyl,tert-butyl, methoxy, ethoxy, i-propoxy, tert-butoxy, trifluoromethyl ortrifluoromethoxy.

Y⁴ and Y⁵ furthermore together with the carbon atoms to which they areattached very particularly preferably represent a six-memberedunsaturated cycle which may optionally be monosubstituted by fluorine,chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy,cyano or nitro.

Y¹ and Y² furthermore together with the carbon atom to which they areattached very particularly preferably represent a cyclobutyl radical.

Z very particularly preferably represents hydrogen, methyl, ethyl,allyl, propargyl, cyclopropyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, methoxymethyl,ethoxymethyl, represents phenyl, benzyl, pyridylmethyl, thiazolylmethyl,each of which is optionally mono- or disubstituted by fluorine,chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy,cyano or nitro or represents the groups

-   -   or cyano.

R¹ very particularly preferably represents hydrogen (but not in theradicals —CO₂R¹ and —SO₂R¹), methyl, ethyl, propyl, isopropyl, n-, s-,i- or t-butyl, allyl, propargyl, cyclopropyl, cyclopentyl, cyclohexyl,represents phenyl or benzyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, methoxy,trifluoromethyl, trifluoromethoxy, cyano or nitro.

R² very particularly preferably represents hydrogen, methyl, ethyl,propyl, isopropyl, allyl, propargyl, methoxy, ethoxy, allyloxy orrepresents benzyloxy which is optionally mono- or disubstituted byfluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro.

R¹, R² together with the nitrogen atom to which they are attached mayvery particularly preferably represent a pyrrolidine, thiazine,piperidine or morpholine radical.

R⁵ very particularly preferably represents hydrogen, methyl or ethyl.

R⁷ very particularly preferably represents methyl, ethyl, propyl,isopropyl, n-, s-, i- or t-butyl, vinyl, trifluoromethyl, methoxy,ethoxy, propoxy, isopropoxy, n-, s-, i- or t-butyloxy, cyclopropyl,cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, representsphenyl, pyridyl or benzyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, n-, s-, i- ort-butyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro or,in the case of the radicals a) and c) mentioned under Ar, alsorepresents a group

or, for the radical g), also represents hydroxyl.

R⁹ very particularly preferably represents hydrogen, methyl, ethyl,propyl, isopropyl, n-, s-, i- or t-butyl, cyclopropyl, cyclopentyl,cyclohexyl, represents phenyl which is optionally mono- or disubstitutedby fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro.

R¹⁰ very particularly preferably represents hydrogen, methyl or ethyl.

R⁹, R¹⁰ together with the nitrogen atom to which they are attached veryparticularly preferably represent a pyrrolidine, piperidine ormorpholine radical.

m very particularly preferably represents 1.

Ar especially preferably represents Ar¹, where Ar¹ represents phenyl,thienyl, pyrimidyl or pyridyl, each of which is optionally mono- totrisubstituted by fluorine, chlorine, bromine, methyl, ethyl, propyl,isopropyl, n-, s-, i- or t-butyl, methoxy, ethoxy, propoxy, isopropoxy,n-, s-, i- or t-butoxy, allyloxy, methallyloxy, 2-butenyloxy,propargyloxy, 2-butinyloxy, methylthio, ethylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl, ethylsulphonyl, trifluoromethyl,difluoromethoxy, trifluoromethoxy, methylenedioxy,difluoromethylenedioxy, tetrafluoroethylenedioxy, difluoromethylthio,trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl,hydroxyl, nitro, mercapto, cyano, amino

-   -   or represents Ar², where Ar² represents Ar¹ which is        additionally substituted by phenyl, benzyloxy or phenoxy, where        these substituents for their part are optionally mono- or        disubstituted by fluorine, chlorine, bromine, methyl, ethyl,        isopropyl, n-, s-, i- or t-butyl, methoxy, ethoxy, isopropoxy,        n-, s-, i- or t-butoxy, trifluoromethyl, trifluoromethoxy, nitro        or cyano.

K especially preferably represents oxygen or sulphur.

V especially preferably represents oxygen or sulphur.

X especially preferably represents CN.

Y¹ and Y³ independently of one another especially preferably representhydrogen, methyl, ethyl or propyl.

Z especially preferably represents hydrogen or methyl.

m especially preferably represents 1.

Y², Y⁴, Y⁵, Y⁶ independently of one another especially preferablyrepresent hydrogen, methyl or ethyl.

All of the compounds of the formula (I) listed above can be present bothas cis- and as trans-isomers. To simplify the presentation, in each caseonly one isomer was shown in the description of the compounds byformulae. However, the invention also refers to the respective otherisomers.

The abovementioned general or preferred radical definitions apply bothto the end products of the formula (I) and, correspondingly, to thestarting materials and intermediates required in each case for thepreparation. These radical definitions can be combined with one anotheras desired, i.e. including combinations between the given preferredranges.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (preferable).

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Special preference according to the invention is given to the compoundsof the formula (I) which contain a combination of the meanings listedabove as being especially preferred.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,can in each case be straight-chain or branched, as far as this ispossible, including in combination with heteroatoms, such as, forexample, in alkoxy.

Unless stated otherwise, optionally substituted radicals can be mono- orpolysubstituted, and in the case of polysubstitutions, the substituentscan be identical or different.

It has been found that the novel compounds of the formula (I) areobtained by the process described below:

(A) compounds of the formula (I),

in which

Ar, V, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above and

K represents oxygen and

Z represents hydrogen,

-   -   are obtained when    -   compounds of the formula (II),    -   in which

Ar and X are as defined above,

are reacted with compounds of the formula (III),

in which

V, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above and

A represents O or S(O)_(q), where q represents 0 or 2, and

R¹¹ represents alkyl, in particular C₁-C₆-alkyl, or benzyl,

if appropriate in the presence of a diluent and if appropriate in thepresence of a base or an acid and/or a metal compound of the formula(IIIa),Me(Q)₂   (IIIa)

in which

Me represents a divalent transition metal atom, in particular nickel,and

Q represents a chelate ligand, in particular a bidentate chelate ligand,such as, for example, acetylacetonate (R. G. Glushkov et al.,Khim.-Farm. Zh. 24, (7), (1990), 24-27; M. V. Mezentseva et al.,Khim.-Farm. Zh. 25, (12), (1991), 19-23; G. Dannhardt, A. Bauer,Pharmazie 51,(1996), 805-810).

(B) Moreover, it has been found that compounds of the formula (I)

in which

Ar, V, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, X and m are as defined above and

K represents oxygen and

Z represents hydrogen

are obtained when compounds of the formula (IV),

in which

Ar and X are as defined above and

Hal represents halogen, in particular chlorine or bromine,

are reacted with compounds of the formula (V),

in which

V, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above,

if appropriate in the presence of a diluent, to give compounds of theformula (VI),

in which

V, Ar, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above,

which are reacted further, if appropriate in the presence of a base andif appropriate in the presence of a trivalent phosphorus compound (forexample triphenylphosphine, triethyl phosphite), with elimination ofsulphur and hydrogen halide, to give compounds of the formula (I)

in which

Ar, V, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above and

K represents oxygen and

Z represents hydrogen

(see A. Eschenmoser et al., Helv. Chim. Acta 54, (1971), 710-734; V.Issartel et al., C.R. Acad. Sci., Ser. II, Mec., Phys., Chim., Astron.321, (12), (1995), 521-524).

(C) Furthermore, it has been found that compounds of the formula (I)

in which

Ar, V, Z, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m and n have one of the meaningsdefined above and

K represents oxygen, but

Z does not represent hydrogen are obtained when

compounds of the formula (VII),

in which

V, Z, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m have one of the meanings given above

and Z does not represent hydrogen,

are reacted with halogenating agents, such as, for example, phosgene,diphosgene and triphosgene, if appropriate in the presence of a diluent,to give compounds of the formula (VIII),

in which

V, Z, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m have one of the meanings given above

and Z does not represent hydrogen and

Hal represents halogen, in particular chlorine or bromine,

-   -   which are then reacted with compounds of the formula (II)    -   in which    -   Ar, X are as defined above,        if appropriate in the presence of a diluent and if appropriate        in the presence of an acid acceptor (see G. Dannhardt, A. Bauer,        Pharmazie 51, (1996), 805-810).

(D) Furthermore, it has been found that compounds of the formula (I),

in which

Ar, V, Z, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m have one of the meanings givenabove and

K represents oxygen, but

Z does not represent hydrogen

are obtained when

compounds of the formula (Ia),

in which

Ar, V, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above,

K represents oxygen,

are reacted with alkylating agents, acylating agents, sulphonylatingagents or condensing agents of the formula (IX),Z-G   (IX)in which

G is a leaving group, such as halogen (in particular iodine, bromine,chlorine), sulphonate (such as, for example, mesylate, triflate ortoluenesulphonate) or alkoxy,

if appropriate in the presence of a solvent and if appropriate in thepresence of a base.

(E) Moreover, it has been found that compounds of the formula (I²),

in which

Ar², V, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, Z and m are as defined above and

K represents oxygen,

are obtained when compounds of the formula (I¹),

in which

Ar¹, V, X, Y¹, Y², Y³, Y⁴, Y⁶, Z and m are as defined above and

Hal represents halogen, in particular bromine,

are reacted with boronic acids of the formula (X),Ar^(2′)—B(OH)₂   (X)in which

Ar^(2′) represents the substituents which are mentioned above under Ar²as additional substituents for Ar¹,

in the presence of a solvent, if appropriate in the presence of a baseand a noble metal complex, preferably a palladium complex.

(F) Furthermore, it has been found that compounds of the formula (I),

in which

Ar, Z, V, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above and

K represents sulphur,

are obtained when compounds of the formula (I),

in which

Ar, Z, V, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above and

K represents oxygen,

are reacted in the presence of a sulphurizing reagent, such as, forexample, phosphorus pentasulphide or2,4-bis-(4-methoxyphenyl)-1,2,3,4-dithiaphosphetane-2,4-disulphide(Lawesson's Reagent) in the presence of a solvent.

(G) Furthermore, it has been found that compounds of the formula (I³),

in which

Ar, K, X, Z, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above and

n represents the number 1 or 2,

are obtained when compounds of the formula (I)

in which

Ar, K, Z, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above and

V represents a sulphur atom,

are oxidized in the presence of peracids (such as, for example,peracetic acid or m-chloroperbenzoic acid) or hydrogen peroxide in thepresence of molybdates or tungstates (such as, for example, ammoniummolybdate or sodium tungstate).

Using according to process A, for example, 4-methyl-benzoylacetonitrileand 2-meth-oxy-2-dihydro-morpholine as starting materials, the course ofthe reaction can be represented by the following equation

Using according to process B, for example,2-bromo-2-(3-chlorobenzoyl)acetonitrile and morpholine-3-thione asstarting materials, the course of the reaction can be represented by thefollowing equation:

Using according to process C, for example,3,4-dichloro-benzoyl-acetonitrile and N-methyl-morpholin-3-one asstarting materials, the course of the reaction can be represented by thefollowing equation:

Using according to process D, for example,3-(4-trifluoromethoxy-phenyl)-2-(1,4-oxazinan-3-ylidene)-3-oxo-propionitrileand 2-chloro-5-chloromethyl-pyridine as starting materials, the courseof the reaction can be represented by the following equation:

Using according to process D, for example,3-(4-trifluoromethyl-phenyl)-2-(1,4-oxazinan-3-ylidene)-3-oxo-propionitrileand 4-chlorobenzoyl chloride as starting materials, the course of thereaction can be represented by the following equation:

Using according to process E, for example,3-(4-bromophenyl)-2-(1,4-oxazinan-3-ylidene)-3-oxo-propionitrile and4-chloro-phenylboronic acid as starting materials, the course of thereaction can be represented by the following equation:

Using according to process F, for example,3-(4-chlorophenyl)-2-(1,4-oxazinan-3-ylidene)-3-oxo-propionitrile andLawesson's Reagent as starting materials, the course of the reaction canbe represented by the following equation

Using according to process G, for example,3-(3,4-dichlorophenyl)-2-(1,4-thioxazinan-3-ylidene)-3-oxo-propionitrileand two equivalents of m-chloroperbenzoic acid (MCPBA) as startingmaterials, the course can be represented by the following equation

Some of the compounds, required as starling materials in process (A), ofthe formula (II),

in which

Ar, X are as defined above,

-   -   are novel and can be prepared by processes known in principle        from the literature (Organikum, 16^(th) revised edition, pp.        415, 417, VEB Deutscher Verlag der Wissenschaften, Berlin 1986).

Among the compounds of the formula (II), the compounds of the formula(II-1-b),

where

T is as defined in the table below Comp. No. T m.p. ° C. II-1-b-1 3-Cl,4-F 78 II-1-b-2 4-Cl, 3-F 87 II-1-b-3 3,5-(CF₃)₂ 91 II-1-b-4 2,4-Cl₂,5-F 106 II-1-b-5 3,5-Cl₂, 4-F 138-140 II-1-b-6 4-Cl, 2-F 90-94 II-1-b-73-CF₃, 5-CH₃ 92 II-1-b-8 3-Cl, 4,5-F₂ 84-88 II-1-b-9 4-CN, 2,5-F₂107-108 II-1-b-10 2,3-F₂ 74 II-1-b-11 3-F, 4-CF₃ 92 II-1-b-123,4-O—CF₂—O 70-73 II-1-b-13 3-NO₂, 5-CF₃ II-1-b-14 4-Cl, 2,5-F₂ 116II-1-b-15 3,4,5-(OC₂H₅)₃ 122 II-1-b-16 4-Br, 2-F 118 II-1-b-17 2,6-Cl₂,4-CF₃ 123 II-1-b-18 2-F, 4-NO₂ 168 II-1-b-19 2,4-Cl₂, 5-NO₂ 100II-1-b-20 4-Cl, 2-F, 5-NO₂ 118 II-1-b-21 2,4-F₂, 5-NO₂ 128 II-1-b-224-Br, 2-F, 5-NO₂ 141 II-1-b-23 2-F, 4-CF₃ 62 II-1-b-24 4-OCF₃, 3-NO₂ 95II-1-b-25 4-Cl, 2-NO₂ 130 II-1-b-26 2-F, 3-CF₃ 67-69 II-1-b-27 2-Cl, 6-F46-48 II-1-b-28 2-Cl, 3-CF₃ 90-93 II-1-b-29 3,4-O—(CF₂)₂—O— 206II-1-b-30 2-Cl, 4-SCH₃ 110 II-1-b-31 2-Cl, 4-SO₂CH₃ 202and the compound of the formula (II-2-b),

where T is as defined in the table below: Comp. No. T m.p. ° C. II-2-b-12,6-Cl₂ >220 II-2-b-2 2,6-Cl₂, 4-CH₃ 95 II-2-b-3 6-Cl 122and the compound of the formula (II-3-b),

where T is as defined in the table below: Comp. No. T m.p. ° C. II-3-b-12-CF₃, 3-(4-Cl′—C₆H₄) oil II-3-b-2 2-CF₃, 3-(2,4-Cl₂′—C₆H₃) oiland the compound No. II-4-b-1

and the compound No. II-5-b-1

are particularly suitable for preparing novel pesticidal, in particularacaricidal, herbicidal and insecticidal, end products. The compounds ofthe formulae II-1-b to II-5-b form part of the subject-matter of anearlier, but not yet published, patent application.

The compounds of the formula (II) are obtained, for example, byhydrolyzing compounds of the formula (XI),

in which

Ar is as defined above,

R¹² represents alkyl, in particular C₁-C₆-alkyl, or benzyl , which mayoptionally be substituted,

-   -   in the presence of an acid (for example an inorganic acid, such        as hydrochloric acid) or a base (for example an alkali metal        hydroxide, such as sodium hydroxide or potassium hydroxide) and,        if appropriate, a diluent (for example an aqueous alcohol, such        as methanol or ethanol) at temperatures between 0° C. and 200°        C., preferably between 20° C. and 150° C., followed by        decarboxylation.

The compounds of the formula (XI) can be prepared by known processes(Organikum, 16^(th) revised edition, pp. 480, VEB Deutscher Verlag derWissen-schaften, Berlin 1986).

The compounds of the formula (XI) are obtained, for example, by reactingcompounds of the formula (XII),

-   -   in which

Ar is as defined above,

-   -   with cyanoacetic esters of the formula (XIII),    -   in which

R¹² represents alkyl, in particular C₁-C₆-alkyl,

-   -   in the presence of a base (for example a metal alkoxide, such as        sodium methoxide or sodium ethoxide) and, if appropriate, in the        presence of a diluent (for example ether or the alcohol derived        from the alkoxide) at temperatures of from 0° C. to 150° C.,        preferably between 20° C. and 120° C.

Some of the compounds of the formula (XII) are novel and can be preparedby processes known in principle (for example Organikum, 16^(th) revisededition, p. 423, VEB Deutscher Verlag der Wissenschaften, Berlin 1986).

The compounds of the formula (XII) are obtained, for example, byreacting compounds of the formula (XIV),

-   -   in which

Ar is as defined above,

-   -   with halogenating agents (for example thionyl chloride,        phosgene, phosphorus trichloride), if appropriate in the        presence of a diluent (for example optionally chlorinated        aliphatic or aromatic hydrocarbons, such as toluene or methylene        chloride) at temperatures from 0° C. to 150° C., preferably        between 20° C. and 100° C.

Cyanoacetic esters of the formula (XIII) are known compounds of organicchemistry.

The compounds, also required as starting materials in process (A), ofthe formula (III),

in which

V, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, R¹¹ and mare as defined above

and

A represents oxygen,

-   -   can be prepared by known processes (J. Köbrösi, P. Berensci,        Chem. Ber., 101, 1979 (1968)).

The compounds of the formula (III) are obtained, for example, byreacting compounds of the formula (VII),

-   -   in which

V, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above

and

Z represents hydrogen,

-   -   with alkylating agents (for example dimethyl sulphate,        triethyloxonium tetra-fluoroborate (Meerwein salt)) at        temperatures of from −20° C. to 150° C., preferably from 0° C.        to 100° C.

Furthermore, the compounds, required as starting materials in process A,of the formula (III),

-   -   in which

V, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, R¹¹ and m are as defined above

-   -   and

A represents sulphur,

-   -   are obtained when compounds of the formula (VII),    -   in which

V, Z, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above

-   -   and

Z represents hydrogen,

-   -   are initially converted with a sulphurizing agent, for example        Lawesson's Reagent, into the thioamide of the formula (V),    -   in which

V, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above,

-   -   in the presence of a solvent, followed by reaction with an        alkylating agent of the formula (XV),        R¹¹-Hal   (XV)    -   in which

R¹¹ is as defined above and

Hal represents halogen, in particular iodine and bromine,

-   -   if appropriate in the presence of a base and in the presence of        a solvent.

The process (A) is characterized in that compounds of the formula (II),in which

Ar, X are as defined above,

-   -   and compounds of the formula (III),    -   in which

R¹¹, V, W, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above,

-   -   are reacted with one another in the presence of a diluent and if        appropriate in the presence of a base.

Suitable diluents for the process (A) are all organic solvents which areinert to the reaction participants. Preference is given to usingoptionally chlorinated aliphatic or aromatic hydrocarbons, such astoluene, xylene, 1,2-dichlorobenzene, chloroform or methylene chloride,furthermore polar solvents, such as dimethyl sulphoxide,dimethylformamide, dimethylacetamide or N-methylpyrrolidone.

Solvents which can also be used are ethers, such as, for example,diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, andalso nitrites, such as, for example, acetonitrile, and esters, such as,for example, ethyl acetate, furthermore also ketones, such as acetone orisopropyl methyl ketone.

Suitable bases for carrying out process (A) are all customary acidacceptors which do not hydrolyze the reaction participants.

Preference is given to using tertiary amines, such as diazabicyclooctane(DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN),triethylamine, pyridine or N,N-dimethylaniline.

It is also possible to use alkoxides, such as sodium methoxide, sodiumethoxide, magnesium ethoxide, potassium tert-butoxide, and metalhydrides, such as sodium hydride, calcium hydride, and also alkali metalor alkaline earth metal carbonates or bicarbonates, such as sodiumbicarbonate, potassium carbonate or sodium carbonate.

Suitable acids for carrying out process (A) are all acids which do nothydrolyze the reaction participants. Preference is given to usingorganic acids, such as p-toluenesulphonic acid and trifluoroacetic acid.

When carrying out the process (A), the reaction temperature can bevaried within a relatively wide range. Advantageously, the reaction iscarried out at temperatures between −20° C. and 160° C., preferablybetween 0° C. and 120° C.

The process (A) is preferably carried out under atmospheric pressure.

When carrying out the process (A), the reaction component of the formula(III) is employed in an equimolar amount or in a relatively large excess(up to 5 mol), preferably in 1.5 to 2 times the molar amount, based onthe reaction component of the formula (II).

The base, which is used if appropriate, is preferably employed in anequimolar amount to the reaction component of the formula (II). Theacid, which is used if appropriate, is preferably employed in catalyticamounts.

The process (B) is characterized in that compounds of the formula (IV)are in each case reacted with thioamides of the formula (V), ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

The starting materials of the formula (IV) can be prepared by knownprocesses (Sequin, Vieles, BSCFAS, Bull. Soc. Chim. Fr. (1956) 1210,1211; Bushey, Hoover, J. Org. Chem. 45, 4198, (1980)). The compounds ofthe formula (V) can be prepared in inert solvents, such as, for example,toluene, from the corresponding keto compound, by using thionylatingagents, in particular P₂S₅ and Lawesson's Reagent (see PreparationExample 4).

Suitable diluents for the process (B) according to the invention are allsolvents which are inert to the compounds of the formula (IV).Preference is given to using hydrocarbons, such as benzine, benzene,toluene, xylene and tetralin, furthermore halogenated hydrocarbons, suchas methylene chloride, chloroform, carbon tetrachloride, chlorobenzeneand o-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, and also strongly polar solvents, such asdimethylformamide, N-methylpyrrolidone, dimethyl sulphoxide andsulpholane.

Suitable acid binders for the reaction according to the process (B)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-di-methylaniline, polymericbases, such as diisopropylaminopolystyrene, furthermore alkaline earthmetal oxides, such as magnesium oxide and calcium oxide, moreover alkalimetal and alkaline earth metal carbonates, such as sodium carbonate,potassium carbonate and calcium carbonate, and also alkali metalhydroxides, such as sodium hydroxide and potassium hydroxide.

Suitable phosphorus reagents for the process (B) according to theinvention are alkyl phosphites, such as triethyl phosphite, tributylphosphite, or triphenylphosphines, such as triphenylphosphine.

The reaction temperature in the process (B) according to the inventioncan be varied within a relatively wide range. In general, the reactionis carried out at temperatures between 0° C. and 200° C., preferablybetween −20° C. and 150° C.

For carrying out the process (B) according to the invention, thestarting materials of the formula (IV) and the thioamide of the formula(V) are generally each employed in approximately equivalent amounts.However, it is also possible to use a relatively large excess of one orthe other component. Work-up is carried out by customary methods.

The process (C) is characterized in that compounds of the formula (VII)are reacted with halogenating agents, such as, for example, phosgene,diphosgene, triphosgene, if appropriate in the presence of a diluent, togive compounds of the formula (VIII) which are then reacted withcompounds of the formula (II), if appropriate in the presence of an acidbinder and if appropriate in the presence of a diluent. The startingmaterials of the formula (VII) can be prepared, for example, by theprocess described by Bushey, Hoover, J. Org. Chem. 45, 4198 (1980).

Suitable acid binders for the reaction according to the process (C)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethylaniline, polymericbases, such as, for example, diisopropylaminopolystyrene, furthermore,alkaline earth metal oxides, such as magnesium oxide and calcium oxide,moreover alkali metal and alkaline earth metal carbonates, such assodium carbonate, potassium carbonate and calcium carbonate, and alsoalkali metal hydroxides, such as sodium hydroxide and potassiumhydroxide.

Suitable diluents for the process (C) according to the invention are allsolvents which are inert to the halogenating agents. Preference is givento using hydrocarbons, such as benzine, benzene, toluene, xylene andtetralin, furthermore halogenated hydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, moreover nitriles, such as acetonitrile, and alsostrongly polar solvents, such as dimethyl sulphoxide and sulpholane.

The reaction temperature in the process (C) according to the inventioncan be varied within a relatively wide range. In general, the reactionis carried out at temperatures between −20° C. and 100° C., preferablybetween 0° C. and 80° C.

The process (C) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (C) according to the invention, thestarting materials of the formula (VII) and the correspondinghalogenating agent are generally each employed in approximatelyequivalent amounts. However, it is also possible to use a relativelylarge excess (up to 3 mol) of one or the other component. Work-up iscarried out by customary methods. In general, precipitated salts areremoved and the reaction mixture that remains is concentrated byremoving the diluent under reduced pressure.

The process (D) is characterized in that compounds of the formula (I) inwhich Ar, V, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above, Krepresents oxygen and Z represents hydrogen are in each case reactedwith alkylating agents, acylating agents, sulphonylating agents orcondensing agents of the formula (IX), if appropriate in the presence ofa diluent and if appropriate in the presence of an acid binder.

The alkylating agents, acylating agents, sulphonylating agents orcondensing agents of the formula (IX) to be used are known chemicals forsynthesis of organic chemistry.

Suitable diluents for the process (D) according to the invention are allsolvents which are inert to the reagents mentioned above. Preference isgiven to using hydrocarbons, such as benzine, benzene, toluene, xyleneand tetralin, furthermore halogenated hydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, and also strongly polar solvents, such as, for example,dimethyl sulphoxide, dimethylformamide, N-methyl-pyrrolidone andsulpholane. The hydrolytic stability of the acylating agents andsulphonylating agents permitting, the reaction can also be carried outin the presence of water.

Suitable acid binders for the reaction according to the process (D)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethylaniline,furthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, moreover alkali metal and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal hydroxides, such as sodium hydroxideand potassium hydroxide, furthermore alkali metal hydrides, such assodium hydride, potassium hydride, or alkali metal alkoxides, such aspotassium tert-butoxide.

The reaction temperatures in the process (D) according to the inventioncan be varied within a relatively wide range. In general, the reactionis carried out at temperatures between −70° C. and +150° C., preferablybetween −20° C. and 100° C.

When carrying out the process (D) according to the invention, thestarting materials of the formula (I) mentioned above and theabovementioned reagents of the formula (IX) are generally each employedin approximately equivalent amounts. However, it is also possible to usea relatively large excess (up to 5 mol) of the above-mentioned reagents.Work-up is carried out by customary methods.

Preferred catalysts for carrying out the process (E) according to theinvention are palladium(0) complexes. Preference is given, for example,to tetrakis(triphenylphosphine)palladium.

Some of the arylboronic acids required for carrying out the process (E)are commercially available, such as, for example, 4-chloro-phenylboronicacid, or they can be prepared by known processes.

Suitable acid acceptors for carrying out the process (E) according tothe invention are inorganic or organic bases. These preferably includealkaline earth metal or alkali metal hydroxides, acetates, carbonates orbicarbonates, such as, for example, sodium hydroxide, potassiumhydroxide, barium hydroxide or ammonium hydroxide, sodium acetate,potassium acetate, calcium acetate or ammonium acetate, sodiumcarbonate, potassium carbonate or ammonium carbonate, sodium bicarbonateor potassium bicarbonate, alkali metal fluorides, such as, for example,cesium fluoride, and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylbenzylamine, pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN).

Suitable diluents for carrying out the process (E) according to theinvention are water, organic solvents and any mixtures thereof. Exampleswhich may be mentioned are: aliphatic, alicyclic or aromatichydrocarbons, such as, for example, petroleum ether, hexane, heptane,cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin;halogenated hydrocarbons, such as, for example, chlorobenzene,dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride,dichloro-, trichloroethane or tetrachloroethylene; ethers, such asdiethyl ether, diisopropyl ether, methyl tert-butyl ether, methyltert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane, diethylene glycol dimethyl ether or anisole;alcohols, such as methanol, ethanol, n- or i-propanol, n-, iso-, sec- ortert-butanol, ethane-diol, propane-1,2-diol, ethoxyethanol,methoxyethanol, diethylene glycol monomethyl ether, diethylene glycolmonoethyl ether; water.

The reaction temperature in the process (E) according to the inventioncan be varied within a relatively wide range. In general, the reactionis carried out a temperatures between 0° C. and +140° C., preferablybetween 50° C. and +100° C.

When carrying out the process (E) according to the invention, theboronic acid of the formula (X) in which Ar^(2′) is as defined above,and compounds of the formula (I¹), in which Ar¹, K, V, X, Y¹, Y², Y³,Y⁴, Y⁵, Y⁶, Z, m and Hal are as defined above, are employed in a molarratio of from 1:1 to 3:1, preferably from 1:1 to 2:1. The catalyst isgenerally employed in amounts of from 0.005 to 0.5 mol, preferably from0.01 to 0.1 mol per mole of the compound of the formula (I¹). The baseis generally employed in excess.

The process (F) is characterized in that compounds of the formula (I) inwhich Ar, V, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, z and m are as defined above andK represents oxygen are reacted with sulphurizing agents, if appropriatein the presence of a diluent.

The sulphurizing agents to be used are known chemicals for synthesis,such as, for example, phosphorus pentasulphide or2,4-bis-(4-methoxyphenyl)-1,2,3,4-dithiaphosphetane-2,4-disulphide(Lawesson's Reagent).

Suitable diluents for the process (F) according to the invention are allsolvents which are inert to the abovementioned reagents. Preference isgiven to using hydrocarbons, such as, for example, benzine, benzene,toluene, xylene and tetralin, furthermore halogenated hydrocarbons, suchas methylene chloride, chloroform, chlorobenzene and o-dichlorobenzene,ethers, such as tetrahydrofuran, dioxane, diisopropyl ether or methyltert-butyl ether.

The reaction temperatures in the process (F) according to the inventioncan be varied within a relatively wide range. In general, the reactionis carried out at temperatures between 0° C. and 250° C., preferablybetween 40° C. and 200° C.

When carrying out the process (F) according to the invention, thestarting materials of the formula (I) and the abovementioned reagentsare generally each employed in approximately equivalent amounts.However, it is also possible to use a relatively large excess of up to 5mol of the abovementioned reagents. Work-up is carried out by customarymethods.

The process (G) is characterized in that compounds of the formula (I) inwhich Ar, K, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined above and Vrepresents a sulphur atom are reacted with an oxidizing agent, such as,for example, peracetic acid, perpropionic acid, perphthalic acid,m-chloroperbenzoic acid or hydrogen peroxide in the presence ofmolybdates or tungstates, in the presence of a diluent which is inert tothe oxidizing agents.

Preferred diluents for the process (G) according to the invention arehalogenated hydrocarbons, such as methylene chloride, chloroform,chlorobenzene, o-dichlorobenzene, furthermore carboxylic esters, such asethyl acetate, or strongly polar solvents, such as dimethyl sulphoxideand sulpholane.

The reaction temperature in the process (G) according to the inventioncan be varied within a relatively wide range. In general, the reactionis carried out at temperatures between −30° C. and 100° C., preferablybetween −10° C. and 80° C.

When carrying out the process (G) according to the invention, thestarting materials of the formula (I) and the oxidizing agent aregenerally employed in a molar ratio of 1:1 or 1:2. However, it is alsopossible to use a relatively large excess (up to 5 mol) of one or theother component. Work-up is carried out by customary methods.

The process (G) according to the invention is generally carried outunder atmospheric pressure.

The active compounds according to the invention are particularlysuitable for use as defoliants, desiccants, haulm-killers and,especially, as weed-killers. By weeds, in the broadest sense, are to beunderstood all plants which grow in locations where they are undesired.Whether the substances according to the invention act as total orselective herbicides depends essentially on the amount used.

The dosages of the active compounds according to the invention requiredfor weed control are between 0.001 and 10 kg/ha, preferably between0.005 and 5 kg/ha.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

According to the invention, it is possible to treat all plants and partsof plants. By plants are to be understood here all plants and plantpopulations such as desired and undesired wild plants or crop plants(including naturally occurring crop plants). Crop plants can be plantswhich can be obtained by conventional breeding and optimization methodsor by biotechnological and genetic engineering methods or combinationsof these methods, including the transgenic plants and including plantcultivars which can or cannot be protected by plant breederscertificates. Parts of plants are to be understood as meaning allabove-ground and below-ground parts and organs of plants, such as shoot,leaf, flower and root, examples which may be mentioned being leaves,needles, stems, trunks, flowers, shoot-bodies, fruits and seeds and alsoroots, tubers and rhizomes. Parts of plants also include harvestedplants and vegetative and generative propagation material, for exampleseedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormulti-layer coating.

The compounds are suitable, depending on the concentration, for thetotal control of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for controllling weeds inperennial cultures, for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, onlawns, turf and pasture-land, and for the selective control of weeds inannual crops.

The active compounds according to the invention are highly suitable forthe selective control of monocotyledonous weeds in dicotyledonous cropsby the pre- and post-emergence method. They can be used verysuccessfully, for example, for the control of harmful grasses in cottonor sugar beet.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspo-emulsionconcentrates, natural and synthetic materials impregnated with activecompound and very fine capsules in polymeric substances.

These formulations are prepared in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, if appropriate with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Suitable liquid solvents areessentially: aromatics, such as xylene, toluene, or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzene, chloroethylene or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example mineral oilfractions, mineral or vegetable oils, alcohols, such as butanol orglycol, and also their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents, such as dimethylformamide and dimethyl sulphoxide, andalso water.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals, such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as finely divided silica,alumina and silicates; suitable solid carriers for granules are: forexample crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, as well as synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks; suitableemulsifiers and/or foam-formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates and proteinhydrolysates; suitable dispersants are: for example lignin-sulphitewaste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%, and in additionpreferably extenders and/or surfactants.

The active compound according to the invention can be present in itscommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, acaricides, nematicides,fungicides, growth-regulating substances or herbicides. The insecticidesinclude, for example, phosphates, carbamates, carboxylates, chlorinatedhydrocarbons, phenylureas and substances produced by microorganisms,inter alia. In preferred embodiments of the present invention, it isalso possible to mix safeners with the compounds according to theinvention, to increase crop plant compatibility.

Examples of particularly advantageous mixing components are thefollowing:

Fungicides:

aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl,bialaphos, binapacryl biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl thiram,tioxymid, tolclofos-methyl tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichiamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

αa-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-fluoro-∃-propyl-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

(E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

1-isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanoneO-(phenylmethyl)-oxime,

1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

1-(3,5-dichlorophenyl)-3-(2-propenyl )-2,5-pyrrolidinedione,

1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

2-aminobutane,

2-bromo-2-(bromomethyl)-pentanedinitrile,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

2-phenylphenol (OPP),

3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,

3,5-dichloro-N-[cyano[(1-methyl-2-propinyl)-oxy]-methyl]-benzamide,

3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

8-hydroxyquinoline sulphate,

9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

potassium hydrogen carbonate,

methanetetrathiol sodium salt,

methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

N-formyl-N-hydroxy-DL-alanine sodium salt,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/acaricides/nematicides:

abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avermectin, AZ60541, azadirachtin, azamethiphos, azinphos A, azinphos M, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,bifenazate, bifenthrin, bioethanomethrin, biopermethrin, BPMC, bromophosA, bufencarb, buprofezin, butathiofos, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin, cloethocarb,clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin,cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl diafenthiuron,diazinon, dichlorvos, diflubenzuron, dimethoat, dimethylvinphos,diofenolan, disulfoton, docusat-sodium, dofenapyn,

eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole,etrimfos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,furathiocarb,

granulosis viruses,

halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,

imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb, methomylmethoxyfenozide, metolcarb, metoxadiazone, mevinphos, milbemectin,monocrotophos,

naled, nitenpyram, nithiazine, novaluron, nuclear polyhedrosis viruses,

omethoat, oxamyl oxydemethon M,

Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoat, phorat, phosalone, phosmet, phosphamidon, phoxim, pirimicarb,pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur, prothiofos,prothoat, pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben,pyridathion, pyrimidifen, pyriproxyfen,

quinalphos,

ribavirin,

salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate,triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron,trimethacarb,

vamidothion, vaniliprole, Verticillium lecanii,

YI 5302,

zeta-cypermethrin, zolaprofos,

(1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

(3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,

1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,

2-(acetlyoxy)-3-dodecyl-1,4-naphthalenedione,

2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

3-methylphenyl propylcarbamate

4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

Bacillus thuringiensis strain EG-2348,

[2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

Herbicides:

acetochlor, acifluorfen(-sodium), aclonifen, alachlor,alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl),benfuresate, bensulfuron(-methyl), bentazone, benzobicyclon, benzofenap,benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium),bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate,cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl),chlornitrofen, chlorsulfuron, chlortoluron, cinidon(-ethyl),cinmethylin, cinosulfuron, clefoxydim, clethodim,clodinafop(-propargyl), clomazone, clomeprop, clopyralid,clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine,cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl),2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba,diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid,diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb,ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen,ethoxysulfuron, etobenzanid, enoxaprop(-P-ethyl), fentrazamide,flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl),flazasulfuron, florasulam, fluazifop(-P-butyl), fluazolate,flucarbazone, flufenacet, flumetsulam, flumiclorac(-pentyl),flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone,fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulfuron(-methyl,-sodium), flurenol(-butyl), fluridone, fluroxypyr(-meptyl),flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen,glufosinate-(-ammonium), glyphosate(-isopropylammonium), halosafen,haloxyfop-(-ethoxyethyl), haloxyfop(-P-methyl), hexazinone,imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic, imazapyr,imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl, -sodium),ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP,mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron,metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron,metribuzin, metsulfuron(-methyl), molinate, monolinuron, naproanilide,napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin,oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen,paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone,phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl),prometryn, propachlor, propanil, propaquizafop, propisochlor,propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate,pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb,pyridate, pyriminobac(-methyl), pyrithiobac(-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl),rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone,sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron,tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide,thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb,tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl),triclopyr, tridiphane, trifluralin and triflusulfuron.

Furthermore, the active compound according to the invention, in itscommercial formulations and in the use forms prepared from theseformulations, can be present as a mixture with synergists. Synergistsare compounds which increase the activity of the active compoundswithout it being necessary for the added synergist to be active itself.

The active compound content of the use forms prepared from thecommercial formulations can vary within wide ranges. The concentrationof active compound in the use forms can be from 0.0000001 to 95% byweight of active compound, preferably between 0.0001 and 1% by weight.

Application is carried out in a customary manner adapted to the useforms.

The active compounds are furthermore suitable for controlling animalpests, preferably arthropods and nematodes, in particular insects andarachnids, which are encountered in agriculture, in forestry, in theprotection of stored products and of materials, and in the hygienesector. They are active against normally sensitive and resistant speciesand against all or some stages of development. The abovementioned pestsinclude:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Blattaria or Orthoptera, for example, Blattaorientalis, Periplaneta americana, Leucophaea maderae, Blattellagermanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoriamigratorioides, Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloxera vastatrix,Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. andLinognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Frankliniellaoccidentalis, Hercinothrips femoralis, Thrips palmi and Thrips tabaci.

From the ordeer of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vasturix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Plutellaxylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.,Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoaspp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua,Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima, Tortrix viridana, Cnaphalocerus spp. and Aulemaoryzae.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Hylotrupes bajulus,Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae,Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis,Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilusspp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchusassimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenusspp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp.,Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor,Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallonsolstitialis, Costelytra zealandica and Lissorhoptus oryzophilus.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Liriomyza spp., Stomoxys spp.,Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibiohortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitiscapitata, Dacus oleae, Tipula paludosa, Hylemnia spp. and Liviomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of the Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp. and Brevipulpus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.Radopholus similis, Ditylenchus dipsaci, Tylenchulus semi penetrans,Heteroderma spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp. and Bursaphelenchusspp.

The active compounds according to the invention have high insecticidaland acaricidal activity after foliar and soil application.

At certain concentrations or application rates, the compounds accordingto the invention also have fungicidal action. Furthermore, they can alsobe used as microbicides or antimycotics.

When used against hygiene pests and pests of stored products, the activecompound has excellent residual activity on wood and clay, and by goodstability to alkali on limed substrates.

The active compounds according to the invention act not only againstplant, hygiene and stored-product pests, but also in the veterinarymedicine sector against animal parasites (ectoparasites), such as hardticks, soft ticks, mange mites, leaf mites, flies (biting and licking),parasitic fly larvae, lice, hair lice, feather lice and fleas. Theseparasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

From the subclass of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Omithodorus spp., Otobiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Stemostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) und Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropods which infest agriculturalproductive livestock, such as, for example, cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys,ducks, geese and bees, other pets, such as, for example, dogs, cats,caged birds and aquarium fish, and also so-called test animals, such as,for example, hamsters, guinea pigs, rats and mice. By controlling thesearthropods, cases of death and reduction in productivity (for meat,milk, wool, hides, eggs, honey etc.) should be diminished, so that moreeconomic and easier animal husbandry is possible by use of the activecompounds according to the invention.

The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injection(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants, by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of molded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

When used for cattle, poultry, pets and the like, the active compoundsof the formula (I) can be used as formulations (for example powders,emulsions, free-flowing compositions), which comprise the activecompounds in an amount of 1 to 80% by weight, directly or after 100- to10,000-fold dilution, or they can be used as a chemical bath.

It has furthermore been found that the compounds of the formula (I)according to the invention also have a strong insecticidal actionagainst insects which destroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout a limitation:

Beetles, such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobiumrufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Ernobius mollis,Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis,Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus spec., Tryptodendron spec., Apate monachus,Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. andDinoderus minutus.

Hymenopterons, such as

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus and Urocerusaugur.

Termites, such as

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermeslucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis andCoptotermes formosanus.

Bristletails, such as

Lepisma saccarina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cardboards, leather, wood and processed wood productsand coating compositions.

Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

Wood and processed wood products which can be protected by the agentsaccording to the invention or mixtures comprising these are to beunderstood as meaning, for example: building timber, wooden beams,railway sleepers, bridge components, boat jetties, wooden vehicles,boxes, pallets, containers, telegraph poles, wood panelling, woodenwindows and doors, plywood, chipboard, joinery or wooden products whichare used quite generally in house-building or in building joinery.

The active compounds can be used as such, in the form of concentrates orin generally customary formulations, such as powders, granules,solutions, suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersing agent and/or binder or fixing agent, awater repellent, if appropriate siccatives and UV stabilizers and ifappropriate dyestuffs and pigments, and also other processingauxiliaries.

The insecticidal compositions or concentrates used for the protection ofwood and timber products comprise the active compound according to theinvention in a concentration of 0.0001 to 95% by weight, in particular0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thenature and occurrence of the insects and on the medium. The optimumamount employed can be determined for the use in each case by a seriesof tests. In general, however, it is sufficient to employ 0.0001 to 20%by weight, preferably 0.001 to 10% by weight, of the active compound,based on the material to be protected.

Solvents and/or diluents which are used are an organochemical solvent orsolvent mixture and/or an oily or oil-like organochemical solvent orsolvent mixture of low volatility and/or a polar organochemical solventor solvent mixture and/or water, and if appropriate an emulsifier and/orwetting agent.

Organochemical solvents which are preferably used are oily or oil-likesolvents having an evaporation number above 35 and a flashpoint above30° C., preferably above 45° C. Substances which are used as such oilyor oil-like water-insoluble solvents of low volatility are appropriatemineral oils or aromatic fractions thereof, or solvent mixturescontaining mineral oils, preferably white spirit, petroleum and/oralkylbenzene.

Mineral oils having a boiling range from 170 to 220° C., white spirithaving a boiling range from 170 to 220° C., spindle oil having a boilingrange from 250 to 350° C., petroleum and aromatics having a boilingrange from 160 to 280° C., terpentine oil and the like, areadvantageously employed.

In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-like solvents of low volatility which have anevaporation number above 35 and a flashpoint above 30° C., preferablyabove 45° C., can be replaced in part by organochemical solvents of highor medium volatility, providing that the solvent mixture likewise has anevaporation number above 35 and a flashpoint above 30° C., preferablyabove 45° C., and that the insecticide/fungicide mixture is soluble oremulsifiable in this solvent mixture.

According to a preferred embodiment, some of the organochemical solventor solvent mixture is replaced by an aliphatic polar organochemicalsolvent or solvent mixture. Aliphatic organochemical solvents containinghydroxyl and/or ester and/or ether groups, such as, for example, glycolethers, esters or the like, are preferably used.

Organochemical binders which are used in the context of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se, are water-dilutable and/or are soluble or dispersible oremulsifiable in the organochemical solvents employed, in particularbinders consisting of or comprising an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenolic resin, hydrocarbon resin, such as indene-cumarone resin,silicone resin, drying vegetable oils and/or drying oils and/orphysically drying binders based on a natural and/or synthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Bitumen or bituminous substances canalso be used as binders in an amount of up to 10% by weight. Dyestuffs,pigments, water-repelling agents, odour correctants and inhibitors oranticorrosive agents and the like which are known per se canadditionally be employed.

It is preferred according to the invention for the composition orconcentrate to comprise, as the organochemical binder, at least onealkyd resin or modified alkyd resin and/or one drying vegetable oil.Alkyd resins having an oil content of more than 45% by weight,preferably 50 to 68% by weight, are preferably used according to theinvention.

All or some of the binder mentioned can be replaced by a fixing agent(mixture) or a plasticizer (mixture). These additives are intended toprevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

The plasticizers originate from the chemical classes of phthalic acidesters, such as dibutyl dioctyl or benzyl butyl phthalate, phosphoricacid esters, such as tributyl phosphate, adipic acid esters, such asdi-(2-ethylhexyl) adipate, stearates, such as butyl stearate or amylstearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

Fixing agents are based chemically on polyvinyl alkyl ethers, such as,for example, polyvinyl methyl ether or ketones, such as benzophenone orethylenebenzophenone.

Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the abovementionedorganochemical solvents or diluents, emulsifiers and dispersing agents.

Particularly effective preservation of wood is achieved by impregnationprocesses on a large industrial scale, for example vacuum, double vacuumor pressure processes.

The ready-to-use compositions can also comprise other insecticides, ifappropriate, and also one or more fungicides, if appropriate.

Possible additional mixing components are, preferably, the insecticidesand fungicides mentioned in WO 94/29 268. The compounds mentioned inthis document are an explicit constituent of the present application.

Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permthrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron and triflumuron, and also fungicides, such asepoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole,cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid,3-iodo-2-propinyl-butyl carbamate, N-octyl-isothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

The active compounds according to the invention can be used particularlyeffectively for controlling plant-damaging insects, such as, forexample, against the larvae of the mustard beetle (Phaedon cochleariae),against the larvae of the green rice leafhopper (Nephotettix cincticeps)and against the larvae of the green peach aphid (Myzus persicae).

In addition to the acaricidal, herbicidal and insecticidal propertiesdescribed, a fungicidal activity of the active compounds according tothe invention is noticeable. In both ‘in vitro’ and ‘in vivo’ studies, abroad fungicidal effect can be observed.

Moreover, it was noticed that the active compounds are, in particular,also suitable for controlling mildew, leaf blotch and Fusaria on theinfected plants.

The preparation and the use of the active compounds according to theinvention is shown in the examples below.

PREPARATION EXAMPLES Example 1

Comp. No. I-1-a-1

A mixture of 1.75 g of 5-ethyl-2-methyl-5,6-dihydro-2H-1,4-oxazin-3-ylmethyl sulphide and 1.80 g of 4-chlorobenzoylacetonitrile in 10 ml oftoluene is heated to 110° C. The reaction is monitored by thin-layerchromatography. Once the starting materials have been convertedvirtually completely, the mixture is cooled and the compounds containedtherein are separated column-chromatographically over a silica gel phaseusing hexane/ethyl acetate (2:1) as mobile phase.

One of the main fractions gave, after evaporation of the solvent, 0.25 g(8.3% of theory) of3-(4-chlorophenyl)-2-(5-ethyl-2-methyl-1,4-oxazinon-3-ylidene)-3-oxopropionitrileof melting point 136° C.

¹H-NMR (400 MHz, d₆-DMSO): δ=0.97 (t, 3H, CH₂—CH ₃); 1.62 (d, 3H,CHCH₃); 4.76 (m, 1H, O—CH—CH₃); 7.56, 7.7 (2AA′BB′, 4H, ArH); 12.4 (s,1H, NH) ppm.

Example 2

Comp. No. I-1-a-2

A mixture of 0.6 g of3-[3,5-bis(trifluoromethyl)phenyl]-2-(2-methyl-1,4-oxazinan-3-ylidene)-3-oxopropionitrileand 0.5 g of Lawesson's Reagent is heated under reflux for 2 hours. Thereaction products in the mixture are then separatedcolumn-chromatographically over a silica gel phase using hexane/ethylacetate (2:1) as mobile phase.

One of the main fractions gives, after evaporation of the solvent, 0.5 g(85% of theory) of3-[3,5-bis(trifluoromethyl)phenyl]-2-(2-methyl-1,4-oxazinan-3-ylidene)-3-thioxopropionitrileof melting point 195° C.

Example 3

Comp. No. III-1

At 0° C., 8.5 g of KOH are added to 10.6 g of5-ethyl-2-methyl-3-morpholinethione in 150 ml of acetone. The mixture iswarmed to room temperature (20° C.) and 5 ml of methyl iodide are added.The mixture is allowed to react for four hours, and the solvent is thendistilled off under reduced pressure. The solid residue that remains isseparated column-chromatographically over a silica gel phase usinghexane/ethyl acetate (10:1).

The main fraction gave, after evaporation of the solvent, 7.6 g (65.5%of theory) of 5-ethyl-2-methyl-5,6-dihydro-2H-1,4-oxazin-3-yl methylsulphide as a yellow oil.

Example 4

Comp. No. V-1

At room temperature (20° C.), a mixture of 20 g of5-ethyl-2-methyl-3-morpholinone and 100 ml of toluene is admixed with 33g of Lawesson's Reagent. The reaction mixture is then heated at refluxfor 24 hours. Work-up is carried out analogously to Example 2.

This gives 11.2 g (50% of theory) of 5-ethyl-2-methyl-3-morpholinethioneas an oil.

Example 5

Comp. No. I-2-A-a-1

A mixture of 1.0 g of 6-chloro-3-pyridinylacetonitrile, 1.27 g of5,6-dihydro-2H-1,4-oxazin-3-yl methyl sulphide (preparation analogous toExample 3) and 10 ml of toluene is heated to 80° C. and stirred at thistemperature for 5 hours. The solvent is then distilled off under reducedpressure, giving a solid residue which is recrystallized from a mixtureof methyl tert-butyl ether (MTBE) and cyclohexane. The resulting solidof melting point 179° C. is dried.

This gives 1.24 g (85.2% of theory) of3-(6-chloro-3-pyridinyl)-2-(1,4-oxazinan-3-ylidene)-3-oxopropionitrile.

Example 6

Comp. No. I-1-a-15

0.5 g of3-[3,5-bis(trifluoromethyl)phenyl]-2-(1,4-thiazinan-3-ylidene)-3-oxo-propionitrile(Comp. No. I-1-a-10) is introduced into 20 ml of chloroform and, at 20°C., admixed with 0.35 g of 3-chloroperbenzoic acid. The progress of thereaction was monitored by thin-layer chromatography. After all of thestarting material has been converted, the reaction product is extractedwith an NaHCO₃ solution and separated column-chromatographically over asilica gel phase using dichloromethane/ethyl acetate (10:1) as mobilephase. The main fraction gives, after evaporation of the solvent, 0.50 gof3-[3,5-bis(trifluoromethyl)phenyl]-2-(1,1-dioxo-1λ⁶,4-thiazinan-3-ylidene)-3-oxo-propionitrilehaving a melting range of from 224 to 226° C.

Example 7

Comp. No. I-1-a-37

Under argon, 1.2 g of3-(3-bromo-5-trifluoromethylphenyl)-2-(2-methyl-1,4-oxazinon-3-ylidene)-3-oxopropionitrile(Comp. No. I-1-a-24) are added to 30 ml of dimethoxyethane and admixedwith 0.5 g of 4-chlorophenylboronic acid, 200 mg oftetrakis-triphenylphosphine and 30 ml of a 2 molar K₂CO₃ solution. Thereaction mixture is heated at 80° C. overnight.

The compounds contained in the reaction mixture are then separatedcolumn-chromatographically over a silica gel phase using hexane/ethylacetate (2:1) as mobile phase.

One of the main fractions gave, after evaporation of the solvent, 0.65 g(52% of theory) of3-[3-(4-chlorophenyl)-5-trifluoromethylphenyl]-2-(2-methyl-1,4-oxazinon-3-ylidene)-3-oxopropionitrileof melting point 119° C.

Analogously to Example 1 and Example 2, and in accordance with thegeneral statements on the preparation of compounds of the formula(I-1-a), the following compounds are obtained:

m.p. Comp. No. K A m Y¹ Y² Y³ Y⁴ Y⁵ Y⁶ V Z ° C. I-1-a-3 O 4-Cl 1 H HC₂H₅ H H H O H Oil I-1-a-4 O 4-(4-Cl—C₆H₄), 2-F 1 H H H H H H O H 198I-1-a-5 O 4-Cl 1 H H H H H H O H 192 I-1-a-6 O 2-CF₃ 1 H H H H H H O H158 I-1-a-7 O 3,5-(CF₃)₂ 1 H H H H H H O H 164 I-1-a-8 O 2,4-F₂ 1 H H HH H H O H 179 I-1-a-9 O 4-CN 1 H H H H H H O H 224 I-1-a-10 O 3,5-(CF₃)₂1 H H H H H H S H 182 I-1-a-11 O 3,5-(CF₃)₂ 1 H H CH₃ CH₃ H H O H OilI-1-a-12 O 3,5-(CF₃)₂ 1 H H C₂H₅ H H H O H Oil I-1-a-13 O 3,5-(CF₃)₂ 1CH₃ H C₂H₅ H H H O H  72 I-1-a-14 O 3,5-(CF₃)₂ 1 CH₃ H H H H H O H 142I-1-a-15 O 3,5-(CF₃)₂ 1 CH₃ H H H H H SO₂ H 224-226 I-1-a-16 O 4-Cl 1 HH CH₃ CH₃ H H O H 102 I-1-a-17 O 4-Cl 1 H H H H CH₃ H O H 235 I-1-a-18 O3,5-(CF₃)₂ 1 H H H H CH₃ H O H 157 I-1-a-19 O 3,5-(CF₃)₂ 1 CH₃ H H H CH₃H O H 142 I-1-a-20 O 4-Cl 1 CH₃ H H H CH₃ H O H 179 I-1-a-21 O 4-Me 1CH₃ H H H H H O H Oil I-1-a-22 O 4-Cl 1 H H H H H H S H 182-184 I-1-a-23O 3-(3-Cl—C₆H₄—O), 5-NO₂ 1 CH₃ H H H H H O H I-1-a-24 O 3-Br, 5-CF₃ 1CH₃ H H H H H O H 126 I-1-a-25 O 3,5-(CH₃)₂ 1 CH₃ H H H H H O H OilI-1-a-26 O 3,5-Br₂ 1 CH₃ H H H H H O H 211 I-1-a-27 O 3,5-Br₂ 1 H H H HH H O H 226 I-1-a-28 O 4-Br, 2-F 1 H H H H H H O H 192 I-1-a-29 O 4-Cl 1CH₃ H H H H H O H 194 I-1-a-30 S 4-Cl 1 H H H H H H O H 194 I-1-a-31 S3,5(CF₃)₂ 1 H H H H H H O H 217 I-1-a-32 O 4-Cl 1 CH₃ CH₃ H H H H S H191 I-1-a-33 O 3,5-(CF₃)₂ 1 CH₃ CH₃ H H H H S H 142 I-1-a-34 O 4-Cl 1—(CH₂)₃— H H H H S H 171 I-1-a-35 O 3,5-(CF₃)₂ 1 —(CH₂)₃— H H H H S H156 I-1-a-36 O 3-CF₃-5-(4-CF₃—C₆H₄) 1 CH₃ H H H H H O H 146 I-1-a-37 O3-CF₃-5-(4-Cl—C₆H₄) 1 CH₃ H H H H H O H 119

Analogously to Example 5 and in accordance with the general statementson the preparation of the compounds of the formula (I-1-a), thefollowing compounds of the formula (I-2-a) are obtained. (I-2-A-a)

(I-2-B-a) Comp. No. K A m Y¹ Y² Y³ Y⁴ Y⁵ Y⁶ V m.p. °C. I-2-A-a-2 O4,6-Cl₂ 1 H H H H H H O 140 I-2-A-a-2 O 2-Cl 1 H H H H H H O 164I-2-A-a-4 O 6-Cl 1 H H CH₃ CH₃ H H O I-2-A-a-5 O 2-Cl 1 CH₃ H H H H H O140 I-2-A-a-6 O 4,6-Cl 1 CH₃ H H H H H O 108 I-2-A-a-7 O 6-Cl 1 CH₃ H HH H H O 189 I-2-B-a-1 O 2.6-Cl₂ 1 CH₃ H H H H H O 174

Example

Phaedon larvae Test

Solvent: 31 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration andpopulated with larvae of the mustard beetle (Phaedon cochleariae) whilethe leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity: I-1-a-10.

Example

Spodoptera frugiperda Test

Solvent: 31 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

A stated amount of the preparation of active compound of the desiredconcentration is pipetted onto a standardized amount of synthetic feed.In 6 repetitions, in each case one larva (L3) of the army worm(Spodoptera frugiperda) is placed on the feed.

After the desired period of time, the kill in % is determined. 100%means that all animals have been killed; 0% means that none of theanimals have been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity: I-1-a-14.

Example

Heliothis virescens Test

Solvent: 30 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Soya bean shoots (Glycine max) are treated by being dipped into thepreparation of active compound of the desired concentration andpopulated with Heliothis virescens caterpillars while the leaves arestill moist.

After the desired period of time, the kill in % is deterrnined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity: I-1-a-14.

Example

Tetranychus Test (OP Resistent/Dip Treatment)

Solvent: 30 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Bean plants (Phaseolus vulgaris) which are heavily infested by allstages of the common spider mite (Tetranychus urticae) are dipped into apreparation of active compound of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all spider mites have been killed; 0% means that none of thespider mites have been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity: I-1-a-10, I-1-a-7.

Example

Post-Emergence Test Solvent: 5 parts by weight of acetone Emulsifier: 1part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants of a height of 5 to 15 cm are sprayed with the preparationof active compound such that the particular amounts of active compounddesired are applied per unit area. After 3 weeks, the degree of damageto the plants is rated in % damage in comparison to the development ofthe untreated control.

The figures denote:  0% = no effect (like untreated control) 100% =total destruction

In this test, for example, the compounds of Preparation ExamplesI-1-a-7, I-1-a-8, I-1-a-9 exhibit strong activity against weeds, andsome of them are tolerated well by crop plants, such as, for example,wheat.

Example

Pre-Emergence Test Solvent: 5 parts by weight of acetone Emulsifier: 1part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours,watered with the preparation of active compound. The amount of water perunit area is advantageously kept constant. The concentration of activecompound in the preparation is immaterial, only the active compoundapplication rate per unit area matters. After three weeks, the degree ofdamage to the plants is rated in % damage in comparison to thedevelopment of the untreated control.

The figures denote:  0% = no effect (like untreated control) 100% =total destruction

In this test, for example, the compounds of Preparation ExamplesI-1-a-3, I-1-a-7, I-1-a-8, I-1-a-9 exhibit strong activity againstweeds, and some of them are tolerated well by crop plants, such as, forexample, wheat and soya.

1-9. (canceled)
 10. A compound of the Formula (I)

wherein K represents oxygen or sulphur, Ar represents in each casesubstituted phenyl or naphthyl or represents in each case optionallysubstituted mono- or bicyclic hetaryl having 5 to 10 ring atoms, Vrepresents the groups —S(O)_(n)— or >N—W W represents hydrogen,optionally substituted alkyl alkenyl alkinyl cyclo-alkylcycloalkyl-alkyl alkoxyalkyl alkoxy, phenylalkyloxy, phenyl phenylalkylhetaryl hetarylalkyl or represents the groups —COR¹,

or cyano, X represents CN,

Y¹ and Y³ independently of one another represent hydrogen, halogen or ineach case optionally substituted alkyl alkoxy, alkoxyalkyl phenylphenylalkyl hetaryl hetarylalkyl or represent the groups

Y², Y⁴, Y⁶ independently of one another represent hydrogen, halogen oroptionally substituted alkyl Y⁵ represents hydrogen or in each caseoptionally substituted alkyl or phenyl or Y⁴ and Y⁵ together with thecarbon atoms to which they are attached represent an optionallysubstituted saturated or unsaturated cycle which is optionallyinterrupted by heteroatoms, or Y¹ and Y² together with the carbon atomto which they are attached represent an optionally substituted cyclewhich is optionally interrupted by heteroatoms, Z represents hydrogen,represents in each case optionally substituted alkyl alkenyl alkinylcycloalkyl cycloalkyl-alkyl alkoxyalkyl phenoxy-alkylphenylalkyl-oxyalkyl phenylthioalkyl phenylalkyl-thioalkyl phenylphenylalkyl hetaryl hetaryl-alkyl or represents the groups

or cyano, l represents 0 to 3, m represents 0 to 2, n represents 0 to 2,R¹ represents hydrogen, represents in each case optionally substituted,saturated or unsaturated alkyl or cycloalkyl each of which is optionallyinterrupted by heteroatoms, represents in each case optionallysubstituted phenyl or hetaryl represents in each case optionallysubstituted phenylalkyl or hetarylalkyl R² represents hydrogen,represents in each case optionally substituted, saturated or unsaturatedalkyl or alkoxy, represents in each case optionally substituted phenylphenylalkyl or phenylalkyloxy, R¹, R² furthermore together with thenitrogen atom to which they are attached may represent an optionallysubstituted cycle which is optionally interrupted by heteroatoms, or R³represents hydrogen, represents in each case optionally substitutedalkyl or alkoxy, represents in each case optionally substituted phenylor phenylalkyl R⁴ represents hydrogen or represents optionallysubstituted alkyl and R⁵, R⁶ independently of one another representhydrogen or represent optionally substituted alkyl.
 11. A compoundaccording to claim 10, wherein Ar represents Ar¹, where Ar¹ representssubstituted phenyl or naphthyl or represents optionally substitutedmono- or bicyclic hetaryl having five to ten ring atoms, each of whichsubstituted radical is optionally mono- to pentasubstituted by halogen,C₁-C₈-alkyl C₂-C₈-alkenyl C₂-C₈-alkinyl C₁-C₈-alkoxy, C₂-C₈-alkenyloxy,C₃-C₈-alkinyloxy, C₁-C₈-alkylthio, C₁-C₆-alkylsulphinyl,C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkyl, C₁-C₆-halogeno-alkoxy,C₂-C₈-halogenoalkenyloxy, C₁-C₂-alkylidenediyl-dioxy,C₁-C₂-halogenoalkylidenediyl-dioxy, halogeno-C₁-C₄-alkylthio,halogeno-C₁-C₄-alkylsulphinyl halogeno-C₁-C₄-alkylsulphonyl hydroxylmercapto, nitro, cyano, amino or by the groups

or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl naphthyl five- or six-membered hetarylphenyl-C₁-C₄-alkyl phenyl-C₁-C₄-alkoxy, phenyl-C₁-C₄-alkyl-S(O)_(p)—,five- or six-membered hetaryl-C₁-C₄-alkoxy, five- or six-memberedhetaryl-C₁-C₄-alkyl-S(O)_(p)—, phenoxy, phenyl-S(O)_(p)—, five- orsix-membered hetaryloxy or hetaryl-S(O)_(p)—, where these substituentsfor their part are in each case optionally mono- to tetrasubstituted byhalogen, C₁-C₆-alkyl C₁-C₆-alkoxy, C₁-C₄-halogenoalkylC₁-C₄-halogenoalkoxy, nitro or cyano, K represents oxygen or sulphur, Lrepresents oxygen or sulphur, V represents the groups —S(O)_(n)—or >N—W, W represents hydrogen, represents in each case optionallyfluorine- and/or chlorine-substituted C₁-C₈-alkyl C₃-C₈-alkenylC₃-C₈-alkinyl, C₃-C₈-cycloalkyl C₃-C₈-cycloalkyl-C₁-C₂-alkyl,C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₂-C₄-alkyl represents phenylC₁-C₄-phenylalkyl, C₁-C₄-phenylalkyloxy, hetaryl hetarylalkyl each ofwhich is optionally mono- to tetrasubstituted by halogen, C₁-C₆-alkylC₁-C₆-alkoxy, C₁-C₄-halogenoalkyl C₁-C₄-halogenoalkoxy, nitro or cyanoor represents the groups

or cyano, X represents CN,

Y¹ and Y³ independently of one another represent hydrogen, halogen,C₁-C₆-alkyl, C₁-C₄-halogenoalkyl, C₁-C₆-alkoxy,C₁-C₆-alkoxy-C₁-C₂-alkyl, represent phenyl, phenyl-C₁-C₄-alkyl five- orsix-membered hetaryl or five- or six-membered hetaryl-C₁-C₄-alkyl eachof which is optionally mono- to tetrasubstituted by halogen, C₁-C₆-alkylC₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitroor represent the groups

Y², Y⁴, Y⁶ independently of one another represent hydrogen, halogen orrepresent fluorine- and/or chlorine-substituted C₁-C₆-alkyl Y⁵represents hydrogen, represents optionally fluorine-substitutedC₁-C₆-alkyl or represents phenyl which is optionally mono- totetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro, or Y⁴ and Y⁵together with the carbon atoms to which they are attached represent a 5-to 8-membered saturated or unsaturated cycle which may be interrupted by1 to 3 heteroatoms from the group consisting of N, O, S and which mayoptionally be mono- to trisubstituted by halogen, C₁-C₄-alkylC₁-C₄-alkoxy, C₁-C₄-halogenoalkyl C₁-C₄-halogenoalkoxy, cyano or nitro,or Y¹ and Y² together with the carbon atom to which they are attachedrepresent a C₃-C₆-cycloalkyl ring, Z represents hydrogen, represents ineach case optionally fluorine- and/or chlorine-substituted C₁-C₈-alkyl,cyano-C₁-C₆-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkinyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₂-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-halogenoalkoxy-C₁-C₄-alkyl, represents phenoxy-C₁-C₄-alkyl,phenyl-C₁-C₄-alkyloxy-C₁-C₄-alkyl, phenylthio-C₁-C₄-alkyl,phenyl-C₁-C₄-alkylthio-C₁-C₄-alkyl, phenyl, phenyl-C₁-C₄-alkyl, five- orsix-membered hetaryl, five- or six-membered hetaryl-C₁-C₄-alkyl, each ofwhich is optionally mono- to tetrasubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro or cyanoor represents the groups

or cyano, p represents 0 to 2, l represents 0 to 2, R¹ representshydrogen (but not in the radicals —CO₂R¹ and —SO₂R¹), represents in eachcase optionally fluorine- and/or chlorine-substituted C₁-C₁₀-alkyl,C₂-C₁₀-alkenyl, C₃-C₆-alkinyl, represents in each case optionallyfluorine-, chlorine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-substitutedC₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl, in which optionally onemethylene group may be interrupted by oxygen or sulphur, or representsphenyl, pyridyl, thienyl, pyrimidyl, thiazolyl, phenyl-C₁-C₄-alkyl,pyridyl-C₁-C₂-alkyl, thiazolyl-C₁-C₂-alkyl, each of which is optionallymono- to tetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro, R² representshydrogen, represents in each case optionally fluorine- and/orchlorine-substituted C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkinyl,C₁-C₆-alkoxy, C₃-C₆-alkenyl,oxy or represents phenyl, phenyl-C₁-C₄-alkylor phenyl-C₁-C₄-alkoxy, each of which is optionally mono- totetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro, or R¹, R²furthermore together with the nitrogen atom to which they are attachedmay represent a five- to eight-membered cycle in which optionally onemethylene group may be replaced by oxygen or sulphur and which may ineach case optionally be substituted by C₁-C₄-alkyl, R³ representshydrogen, optionally halogen-substituted C₁-C₆-alkyl or representsphenyl or phenyl-C₁-C₂-alkyl, each of which is optionally mono- totetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro, R⁴ representshydrogen or C₁-C₆-alkyl, R⁵, R⁶ independently of one another representhydrogen or optionally fluorine- and/or chlorine-substitutedC₁-C₄-alkyl, R⁷ represents in each case optionally fluorine- and/orchlorine-substituted C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₃-C₁₀-alkinyl,C₁-C₁₀-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, ineach case optionally fluorine-, chlorine-, C₁-C₄-alkyl- and/orC₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl or C₃-C₈-cycloalkoxy, in whichoptionally one methylene group may be replaced by oxygen or sulphur,represents phenyl, phenoxy, benzyloxy, five- or six-membered hetaryl orphenyl-C₁-C₄-alkyl, each of which may optionally be mono- totetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogeno-alkyl, C₁-C₄-halogenoalkoxy, cyano or nitro or, in thecase of the radicals a) and c) mentioned under Ar, also represents agroup

or, for the radical g), also represents hydroxyl, R⁸ represents hydrogenor C₁-C₄-alkyl, R⁹ represents hydrogen, in each case optionallyfluorine- and/or chlorine-substituted C₁-C₁₀-alkyl, C₃-C₈-alkenyl,C₃-C₈-alkinyl, C₁-C₁₀-alkoxy, C₃-C₈-alkenyloxy, optionally fluorine-,chlorine-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl, inwhich optionally one methylene group may be replaced by oxygen orsulphur, represents phenyl, phenyl-C₁-C₄-alkyl or phenyl-C₁-C₂-alkoxy,each of which may optionally be mono- to tetrasubstituted by halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,cyano or nitro, R¹⁰ represents hydrogen, C₁-C₆-alkyl, or C₃-C₆-alkenyl,or R⁹, R¹⁰ furthermore together with the nitrogen atom to which they areattached may represent an optionally C₁-C₄-alkyl-substituted five- toeight-membered cycle in which optionally one methylene group may bereplaced by oxygen or sulphur, m represents 0 to 2, and n represents 0to
 2. 12. A compound according to claim 10, wherein K represents oxygenor sulphur, Ar represents Ar¹, where Ar¹ represents substituted phenyl,naphthyl, quinolinyl, thienyl, pyrimidyl, furanyl, thiazolyl,benzothiazolyl, oxazolyl, pyrazolyl, or pyridyl, each of which isoptionally mono- to trisubstituted by fluorine, chlorine, bromine,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkoxy,C₃-C₆-alkenyloxy, C₃-C₆-alkinyloxy, C₁-C₆-alkylthio,C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-halogenoalkyl,C₁-C₄-halogeno-alkoxy, C₂-C₄-halogenoalkenyloxy,C₁-C₂-alkylidenediyl-dioxy, C₁-C₂-halogenoalkylidenediyl-dioxy,halogen-C₁-C₂-alkylthio, halogen-C₁-C₂-alkylsulphinyl,halogen-C₁-C₂-alkylsulphonyl, hydroxyl, mercapto, nitro, cyano, amino orby one of the following groups

or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl, pyridyl, pyrimidyl, thienyl, furanyl, thiazolyl,tetrazolyl, triazolyl, benzyl, phenyl-C₁-C₂-alkoxy,phenyl-C₁-C₂-alkyl-S(O)_(p)—, thienyl-C₁-C₂-alkoxy,thiazolyl-C₁-C₂-alkoxy, pyrimidyl-C₁-C₂-alkoxy,thiazolyl-C₁-C₂-alkyl-S(O)_(p)—, pyridyl-C₁-C₂-alkyl-S(O)_(p), phenoxy,phenyl-S(O)_(p)—, pyridyloxy, pyrimidyloxy, thiazolyloxy,pyridyl-S(O)_(p)—, pyrimidyl-S(O)_(p)— or thiazolyl-S(O)_(p)—, wherethese substituents for their part are optionally mono- to trisubstitutedby fluorine, chlorine, bromine, C₁-C₄-alkyl, C₂-C₄-alkenyl,C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, nitro or cyano,L represents oxygen or sulphur, V represents the groups —S(O)_(n)— or

W represents hydrogen, represents in each case optionally fluorine-and/or chlorine-substituted C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkinyl,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₂-alkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₂-C₃-alkyl, represents phenyl, phenyl-C₁-C₂-alkyl,phenyl-C₁-C₂-alkoxy, pyridyl, thiazolyl, pyrimidyl, thienyl,pyridyl-C₁-C₂-alkyl, pyrimidyl-C₁-C₂-alkyl, thiazolyl-C₁-C₂-alkyl, eachof which is optionally mono- to trisubstituted by fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro or cyano or represents the groups

Y¹ and Y³ independently of one another represent hydrogen, representfluorine, C₁-C₄-alkyl, C₁-C₂-halogenoalkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₂-alkyl, represents phenyl, thienyl, pyridyl,thiazolyl, pyrimidyl, phenyl-C₁-C₂-alkyl, thiazolylmethyl,pyridylmethyl, each of which is optionally mono- to trisubstituted byfluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, cyano or nitro or representthe groups

Y², Y⁴, Y⁶ independently of one another represent hydrogen orC₁-C₄-alkyl, Y⁵ represents hydrogen, represents optionallyfluorine-substituted C₁-C₄-alkyl, or represents phenyl, which isoptionally mono- to trisubstituted by fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,nitro or cyano, or Y⁴ and Y⁵ furthermore together with the carbon atomsto which they are attached represent a 5- or 6-membered saturated orunsaturated cycle which may be interrupted by a heteroatom from thegroup consisting of N, O, S and which may optionally be mono- ordisubstituted by fluorine, chlorine, bromine, methyl, tert-butyl,methoxy, trifluoromethyl, tri-fluoromethoxy, cyano or nitro, or Y¹ andY² together with the carbon atom to which they are attached represent aC₄-C₆-cycloalkyl, ring, Z represents hydrogen, represents in each caseoptionally fluorine- and/or chlorine-substituted C₁-C₆-alkyl,cyano-C₁-C₃-alkyl, C₃-C₆-alkenyl, C₃-C₈-alkinyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₂-alkyl, C₁-C₄-alkoxy-C₁-C₂-alkyl,C₁-C₄-halogeno-C₁-C₂-alkyl, represents phenoxy-C₁-C₂-alkyl,phenyl-C₁-C₂-alkyloxy-C₁-C₂-alkyl, phenyl,thio-C₁-C₂-alkyl,phenyl-C₁-C₂-alkylthio-C₁-C₂-alkyl, phenyl-C₁-C₂-alkyl, phenyl,pyridyl-C₁-C₂-alkyl, thiazolyl-C₁-C₂-alkyl, each of which is optionallymono- to trisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, nitro or cyanoor represents the groups

or cyano, where p represents 0 to 2, R¹ represents hydrogen (but not inthe radicals —CO₂R¹ and —SO₂R¹), represents in each case optionallyfluorine- and/or chlorine-substituted C₁-C₆-alkyl, C₃-C₆-alkenyl,C₃-C₄-alkinyl, represents in each case optionally fluorine-, chlorine-,C₁-C₂-alkyl-, C₁-C₂-alkoxy-substituted C₃-C₆-cycloalkyl or representsphenyl, or benzyl, each of which is optionally mono- or disubstituted byfluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, cyano or nitro, R² representshydrogen, represents in each case optionally fluorine- and/orchlorine-substituted C₁-C₄-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkinyl,C₁-C₄-alkoxy, C₃-C₄-alkenyloxy or represents phenyl, benzyl, benzyloxy,each of which is optionally mono- or disubstituted by fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, cyano or nitro, or R¹, R² furthermore togetherwith the nitrogen atom to which they are attached may represent anoptionally C₁-C₂-alkyl-substituted five- or six-membered cycle in whichoptionally one methylene group may be replaced by oxygen, and R³represents hydrogen, represents C₁-C₄-alkyl, or represents phenyl, orbenzyl, each of which is optionally mono- or disubstituted by fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, trifluoromethyl,difluoromethoxy, trifluoromethoxy, cyano or nitro, R⁵ representshydrogen, methyl, or ethyl, R⁷ represents C₁-C₆-alkyl, C₂-C₆-alkenyl,C₃-C₆-alkinyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₂-alkyl,C₁-C₄-alkylthio-C₁-C₂-alkyl, each of which is optionally substituted byfluorine and/or chlorine, represents C₃-C₆-cycloalkyl, orC₃-C₆-cycloalkoxy in which optionally one methylene group may bereplaced by oxygen and which are in each case optionally substituted byfluorine, chlorine, C₁-C₂-alkyl, and/or C₁-C₂-alkoxy, represents phenyl,phenoxy, benzyl,oxy, thienyl, furanyl, pyridyl, pyrimidyl, thiazolyl,pyrazolyl, or phenyl-C₁-C₂-alkyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro or,in the case of the radicals a) and c) mentioned under Ar, alsorepresents a group

or, for the radical g), also represents hydroxyl, R⁸ representshydrogen, R⁹ represents hydrogen, represents C₁-C₆-alkyl, C₃-C₆-alkenyl,C₃-C₆-alkinyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, in which optionally onemethylene group may be replaced by oxygen and each of which isoptionally substituted by fluorine and/or chlorine, represents phenyl,or phenyl-C₁-C₂-alkyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro, R¹⁰represents hydrogen or C₁-C₄-alkyl, or R⁹, R¹⁰ furthermore together withthe nitrogen atom to which they are attached represent an optionallyC₁-C₂-alkyl-substituted five- or six-membered cycle in which optionallyone methylene group may be replaced by oxygen, m represents 0 or 1, andn represents 0 to
 2. 13. A compound according to claim 10, wherein Krepresents oxygen or sulphur, Ar represents Ar¹, where Ar¹ representssubstituted phenyl, thienyl, pyrimidyl, furanyl or pyridyl, each ofwhich is optionally mono- to trisubstituted by fluorine, chlorine,bromine, methyl, ethyl, propyl, i-propyl, s-, n-, i- or t-butyl,methoxy, ethoxy, propoxy, i-propoxy, s-, n-, i- or t-butoxy, alkyloxy,methallyloxy, 2-butenyloxy, propargyloxy, 2-buti-nyloxy, methylthio,ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,ethylsulphonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy,methylenedioxy, difluoromethylenedioxy, tetrafluoroethylenedioxy,difluoromethylthio, trifluoromethylthio, tri-fluoromethylsulphinyl,trifluoromethylsulphonyl, hydroxyl, mercapto, nitro, cyano, amino, or byone of the following groups

or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl, pyridyl, thienyl, tetrazolyl, triazolyl,benzyloxy, benzylthio, thiazolylmethyloxy, pyridylmethyloxy,pyrimidylmethyloxy, thiazolylmethylthio, pyridylmethylthio, phenoxy orphenylthio, where these substituents for their part are optionally mono-or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, n- ori-propyl, s-, n-, i- or t-butyl, methoxy, ethoxy, i-propoxy, s-, n- ort-butoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano, and Lrepresents oxygen or sulphur, V represents the group —S(O)_(n)—,

X represents Y¹ and Y³ independently of one another represent hydrogen,methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, sec-butyl,tert-butyl, represent phenyl, or benzyl, each of which is optionallymono- to trisubstituted by fluorine, chlorine, bromine, methyl, methoxy,trifluoromethyl, difluoromethoxy or trifluoromethoxy, Y², Y⁴, Y⁶independently of one another represent hydrogen, methyl, or ethyl, Y⁵represents hydrogen, methyl, ethyl, propyl, i-propyl, or representsphenyl, which is optionally mono- or disubstituted by fluorine,chlorine, bromine, methyl, ethyl, i-propyl, tert-butyl, methoxy, ethoxy,i-propoxy, tert-butoxy, trifluoromethyl, or trifluoromethoxy, or Y⁴ andY⁵ together with the carbon atoms to which they are attached represent asix-membered unsaturated cycle which may optionally be monosubstitutedby fluorine, chlorine, bromine, methyl, methoxy, tri-fluoromethyl,trifluoromethoxy, cyano or nitro, or Y¹ and Y² together with the carbonatom to which they are attached represent a cyclobutyl, radical, Zrepresents hydrogen, methyl, ethyl, allyl, propargyl, cyclopropyl,cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl,cyclohexylmethyl, methoxymethyl, ethoxymethyl, represents phenyl,benzyl, pyridylmethyl, thiazolylmethyl, each of which is optionallymono- or disubstituted by fluorine, chlorine, bromine, methyl, methoxy,trifluoromethyl, or trifluoromethoxy, cyano or nitro or represents thegroups

or cyano, where R¹ represents hydrogen (but not in the radicals —CO₂R¹and —SO₂R¹), methyl, ethyl, propyl, isopropyl, n-, s-, i- or t-butyl,allyl, propargyl, cyclopropyl, cyclopentyl, cyclohexyl, representsphenyl, or benzyl, each of which is optionally mono- or disubstituted byfluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro, R² represents hydrogen, methyl, ethyl,propyl, isopropyl, allyl, propargyl, methoxy, ethoxy, alkyloxy orrepresents benzyloxy which is optionally mono- or disubstituted byfluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro, or R¹, R² together with the nitrogenatom to which they are attached may represent a pyrrolidine, thiazine,piperidine or morpholine radical, R⁵ represents hydrogen, methyl, orethyl, R⁷ represents methyl, ethyl, propyl, isopropyl, n-, s-, i- ort-butyl, vinyl, tri-fluoromethyl, methoxy, ethoxy, propoxy, isopropoxy,n-, s-, i- or t-butyloxy, cyclopropyl, cyclopentyl, cyclohexyl,cyclopentyloxy, cyclohexyloxy, represents phenyl, pyridyl, or benzyl,each of which is optionally mono- or disubstituted by fluorine,chlorine, bromine, methyl, n-, s-, i- or t-butyl, methoxy,trifluoromethyl, trifluoromethoxy, cyano or nitro or, in the case of theradicals a) and c) mentioned under Ar, also represents a group

or, for the radical g), also represents hydroxyl, R⁹ representshydrogen, methyl, ethyl, propyl, isopropyl, n-, s-, i- or t-butyl,cyclopropyl, cyclopentyl, cyclohexyl, represents phenyl, which isoptionally mono- or disubstituted by fluorine, chlorine, bromine,methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, R¹⁰represents hydrogen, methyl, or ethyl, R⁹, R¹⁰ together with thenitrogen atom to which they are attached represent a pyrrolidine,piperidine or morpholine radical, m represents 1, and n represents 0 to2.
 14. A compound according to claim 10, wherein Ar represents Ar¹,where Ar¹ represents substituted phenyl, thienyl, pyrimidyl, or pyridyl,each of which is optionally mono- to trisubstituted by fluorine,chlorine, bromine, methyl, ethyl, propyl, isopropyl, n-, s-, i- ort-butyl, methoxy, ethoxy, propoxy, isopropoxy, n-, s-, i- or t-butoxy,allyloxy, methallyloxy, 2-butenyloxy, propargyloxy, 2-butinyloxy,methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,ethylsulphonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy,methylenedioxy, difluoromethylenedioxy, tetrafluoroethylenedioxy,difluoromethylthio, trifluoromethylthio, trifluoromethylsulphinyl,trifluoromethylsulphonyl, hydroxyl, nitro, mercapto, cyano, amino, orrepresents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl, benzyl,oxy or phenoxy, where these substituentsfor their part are optionally mono- or disubstituted by fluorine,chlorine, bromine, methyl, ethyl, isopropyl, n-, s-, i- or t-butyl,methoxy, ethoxy, isopropoxy, n-, s-, i- or t-butoxy, trifluoromethyl,trifluoromethoxy, nitro or cyano, K represents oxygen or sulphur, Vrepresents sulphur, X represents CN, Y¹ and Y³ independently of oneanother represent hydrogen, methyl, ethyl, or propyl, Z representshydrogen or methyl, m represents 1, and Y², Y⁴, Y⁵, Y⁶ independently ofone another represent hydrogen, methyl, or ethyl.
 15. A process forpreparing a compound according to claim 10, selected from the groupconsisting of processes (A), (B), (C), (D), (E), (F) and (G), wherein(A) in said process (A), K represents oxygen and Z represents hydrogen,and said process (A) comprises the step of reacting a compound of theFormula (II),

wherein Ar and X are as defined in claim 10, with a compound of theFormula (III),

wherein V, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined in claim 10, andA represents O or S(O)_(q), where q represents 0 or 2, and R¹¹represents alkyl, in particular C₁-C₆-alkyl, or benzyl, optionally inthe presence of a diluent and optionally in the presence of a base or anacid and/or a metal compound of the Formula (IIIa),Me(Q)₂   (IIIa) wherein Me represents a divalent transition metal atom,optionally nickel, and Q represents a chelate ligand, optionally abidentate chelate ligand, optionally acetylacetonate, or (B) in saidprocess (B), K represents oxygen and Z represents hydrogen, and saidprocess (B) comprises the steps of reacting a compound of the Formula(IV),

wherein Ar and X are as defined in claim 10 and Hal represents halogen,with a compound of the Formula (V),

wherein V, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined in claim 10,optionally in the presence of a diluent, to give a compound of theFormula (VI),

wherein V, Ar, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined claim 10,and, reacting said compound of the Formula (VI) optionally in thepresence of a base and optionally in the presence of a trivalentphosphorus compound with elimination of sulphur and hydrogen halide, togive a compound according to claim 10, in which K represents oxygen andZ represents hydrogen, or (C) in said process (C), K represents oxygenbut Z does not represent hydrogen, and said process (C) comprises thesteps of reacting a compound of the Formula (VII),

wherein V, Z, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined in claim 10and Z does not represent hydrogen, with a halogenating agent, whereinsaid halogenating agent is optionally selected from the group consistingof phosgene, diphosgene, triphosgene, and combinations thereof,optionally in the presence of a diluent, to give a compound of theFormula (VIII),

wherein V, Z, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined in claim 10and Z does not represent hydrogen and Hal represents halogen, andreacting said compound of the Formula (VIII) with a compound of theFormula (II),

wherein Ar, X are as defined in claim 10, optionally in the presence ofa diluent and optionally in the presence of an acid acceptor, or (D) insaid process (D), K represents oxygen but Z does not represent hydrogen,and said process (D) comprises the step of reacting a compound of theFormula (Ia),

wherein Ar, V, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined in claim10, K represents oxygen, with a member selected from the groupconsisting of an alkylating agent, an acylating agent, a sulphonylatingagent and a condensing agent of the Formula (IX),Z-G   (IX) wherein G represents a leaving group, optionally in thepresence of a diluent and optionally in the presence of a base, or (E)in said process (E), K represents oxygen, and said process (E) comprisesthe step of reacting a compound of the Formula (I¹),

wherein Ar¹ is defined in claim 11 and V, X, Y¹, Y², Y³, Y⁴, Y⁶, Z and mare as defined in claim 10 and Hal represents halogen, optionallybromine, with a boronic acid of the Formula (X),Ar^(2′)—B(OH)₂   (X) wherein Ar^(2′) represents the substituents definedin claim 11 under Ar² as additional substituents for Ar¹, in thepresence of a solvent, optionally in the presence of a base and a noblemetal complex, said noble metal complex optionally being a palladiumcomplex, or (F) in said process (F), K represents sulphur, said process(F) comprising the step of reacting a compound of the Formula (I),

wherein Ar, Z, V, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined inclaim 10 and K represents oxygen, with a sulphurizing agent in thepresence of a diluent, or (G) in said process (G), V represents S(O)_(n)and n represents 1 or 2, said process (G) comprising the step ofoxidizing a compound of the Formula (I),

wherein Ar, Z, K, X, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶ and m are as defined inclaim 10 and V represents a sulphur atom, in the presence of a peracidor hydrogen peroxide in the presence of a molybdate or a tungstate. 16.A method for controlling undesirable vegetation and/or animal pests,comprising the step of allowing an effective amount of at least onecompound according to claim 10 to act on a member selected from thegroup consisting of an undesirable plant, an animal pest, a habitat ofsaid undesirable plant, a habitat of said animal pest and combinationsthereof.
 17. A composition, comprising a compound according to claim 10and one or more extenders and/or one or more surfactants.
 18. Thecomposition of claim 17, wherein said composition is a member selectedfrom the group consisting of an herbicidal composition, an acaricidalcomposition, and insecticidal composition and combinations thereof.